CN118908835A - Preparation method of 2-nitro-5-fluoroanisole - Google Patents
Preparation method of 2-nitro-5-fluoroanisole Download PDFInfo
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- WLKUSVNHZXUEFO-UHFFFAOYSA-N 4-fluoro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(F)=CC=C1[N+]([O-])=O WLKUSVNHZXUEFO-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 229910002651 NO3 Inorganic materials 0.000 claims abstract description 11
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- MFJNOXOAIFNSBX-UHFFFAOYSA-N 1-fluoro-3-methoxybenzene Chemical compound COC1=CC=CC(F)=C1 MFJNOXOAIFNSBX-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 6
- 239000012263 liquid product Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract 2
- 238000001704 evaporation Methods 0.000 claims abstract 2
- 230000008020 evaporation Effects 0.000 claims abstract 2
- 238000001914 filtration Methods 0.000 claims abstract 2
- 238000005406 washing Methods 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 4
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims 2
- 230000006837 decompression Effects 0.000 claims 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 3
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 240000001972 Gardenia jasminoides Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229960003278 osimertinib Drugs 0.000 description 1
- DUYJMQONPNNFPI-UHFFFAOYSA-N osimertinib Chemical compound COC1=CC(N(C)CCN(C)C)=C(NC(=O)C=C)C=C1NC1=NC=CC(C=2C3=CC=CC=C3N(C)C=2)=N1 DUYJMQONPNNFPI-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
技术领域Technical Field
本发明涉及有机合成技术领域，具体而言，涉及一种2-硝基-5-氟苯甲醚的制备方法。The invention relates to the technical field of organic synthesis, and in particular to a method for preparing 2-nitro-5-fluoroanisole.
背景技术Background Art
2-硝基-5-氟苯甲醚是一种重要的化工原料，是生产抗癌药物奥希替尼的核心骨架，也是其它药物的重要中间体。广泛用于配制许多花香型香精，特别是栀子、紫丁香、葵花型香精；还用作啤酒的抗氧剂，乙烯聚合物紫外线稳定剂和肠内杀虫剂的原料；也可用于有机合成，香料和驱虫剂、恒温器填充物；在香料制备、有机合成、折射率测定、杀虫剂制备等方面也得到广泛应用。2-Nitro-5-fluoroanisole is an important chemical raw material, the core skeleton of the anticancer drug osimertinib, and an important intermediate for other drugs. It is widely used in the preparation of many floral flavors, especially gardenia, lilac, and sunflower flavors; it is also used as an antioxidant for beer, a UV stabilizer for ethylene polymers, and a raw material for intestinal insecticides; it can also be used in organic synthesis, spices and insect repellents, and thermostat fillers; it is also widely used in the preparation of spices, organic synthesis, refractive index determination, and preparation of insecticides.
现有技术中2-硝基-5-氟苯甲醚的合成虽然有文献报道，但依然存在一些不足之处，比如合成过程需要用到浓硝酸；反应收率过低，最高仅41％；这些不足之处使得制作过程的制作成本高昂，产生的过量酸性废液污染环境，生产过程安全性得不到保障。因此寻找更加绿色经济的方法合成2-硝基-5-氟苯甲醚具有非常重要的意义。Although the synthesis of 2-nitro-5-fluoroanisole in the prior art has been reported in the literature, there are still some shortcomings, such as the need to use concentrated nitric acid in the synthesis process; the reaction yield is too low, the highest is only 41%; these shortcomings make the production cost of the production process high, the excessive acidic waste liquid generated pollutes the environment, and the safety of the production process cannot be guaranteed. Therefore, it is of great significance to find a more green and economical method to synthesize 2-nitro-5-fluoroanisole.
发明内容Summary of the invention
本发明的目的在于提供一种2-硝基-5-氟苯甲醚的制备方法，补充该化合物制备方法的一些不足之处。该发明工艺设备简单，操作容易，对环境友好，成本低，收率较好，可商业化大规模的制备和生产，满足当前不断增长的市场需。The object of the present invention is to provide a method for preparing 2-nitro-5-fluoroanisole, and to supplement some deficiencies of the method for preparing the compound. The invention has simple process equipment, easy operation, environmental friendliness, low cost, good yield, and can be commercially prepared and produced on a large scale to meet the current growing market needs.
本发明的实施例通过以下技术方案实现：The embodiments of the present invention are implemented by the following technical solutions:
具体地：将3-氟苯甲醚溶于溶剂中，控温40-80℃，加入硝酸盐，控温反应6-24h，反应完全后；旋蒸回收溶剂，加入有机溶剂萃取3次，弃掉水相，有机相用饱和食盐水洗涤，无水硫酸镁干燥，过滤，减压蒸除溶剂即得油状液体产物，经进一步纯化得目标产物。Specifically, 3-fluoroanisole is dissolved in a solvent, the temperature is controlled at 40-80°C, nitrate is added, the temperature is controlled to react for 6-24 hours, and after the reaction is complete; the solvent is recovered by rotary evaporation, an organic solvent is added to extract 3 times, the aqueous phase is discarded, the organic phase is washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is evaporated under reduced pressure to obtain an oily liquid product, which is further purified to obtain the target product.
进一步地，所述硝酸盐与3-氟苯甲醚的摩尔比为1:1-3:1。Furthermore, the molar ratio of the nitrate to 3-fluoroanisole is 1:1-3:1.
进一步地，加入溶剂后控温至40-80℃；滴入硝酸盐后控温40-80℃，反应时间6-24h。Furthermore, after adding the solvent, the temperature is controlled to 40-80°C; after dripping the nitrate, the temperature is controlled to 40-80°C, and the reaction time is 6-24h.
进一步地，所述硝酸盐为是硝酸铜、硝酸铁、四甲基硝酸铵中的一种或几种。Furthermore, the nitrate is one or more of copper nitrate, iron nitrate, and tetramethylammonium nitrate.
进一步地，所述溶剂为六氟异丙醇或六氟异丙醇与四氢呋喃、1,4-二氧六环，乙腈，二氯甲烷，1,2-二氯乙烷，乙酸乙酯，二甲苯中的一种或几种。Furthermore, the solvent is hexafluoroisopropanol or hexafluoroisopropanol and one or more of tetrahydrofuran, 1,4-dioxane, acetonitrile, dichloromethane, 1,2-dichloroethane, ethyl acetate, and xylene.
进一步地，纯化时，可采用柱色谱分离、重结晶中的一种或几种。Furthermore, during purification, one or more of column chromatography separation and recrystallization may be used.
进一步地，萃取时萃取溶剂为乙酸乙酯、二氯甲烷或1,2-二氯乙烷中的一种或几种。Furthermore, during extraction, the extraction solvent is one or more of ethyl acetate, dichloromethane or 1,2-dichloroethane.
本发明实施例的技术方案至少具有如下优点和有益效果：The technical solution of the embodiment of the present invention has at least the following advantages and beneficial effects:
本发明合成方法摒弃传统浓硫酸/浓硝酸系统硝化，采用更加绿色环保的硝酸盐作为硝基源，无需过量的原料，工艺设备简单，操作容易，反应条件温和，对环境友好，成本低，收率高，可商业化大规模的制备和生产，满足当前不断增长的市场需求。The synthesis method of the present invention abandons the traditional concentrated sulfuric acid/concentrated nitric acid system nitration, adopts more environmentally friendly nitrate as the nitro source, does not require excessive raw materials, has simple process equipment, easy operation, mild reaction conditions, is environmentally friendly, has low cost, high yield, and can be commercially prepared and produced on a large scale to meet the current growing market demand.
附图说明BRIEF DESCRIPTION OF THE DRAWINGS
为了更清楚地说明本发明实施例的技术方案，下面将对实施例中所需要使用的附图作简单地介绍，应当理解，以下附图仅示出了本发明的某些实施例，因此不应被看作是对范围的限定，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他相关的附图。In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings required for use in the embodiments are briefly introduced below. It should be understood that the following drawings only show certain embodiments of the present invention and therefore should not be regarded as limiting the scope. For ordinary technicians in this field, other related drawings can be obtained based on these drawings without creative work.
图1为本发明实施例2提供的2-硝基-5-氟苯甲醚的氢谱图。FIG. 1 is a hydrogen spectrum of 2-nitro-5-fluoroanisole provided in Example 2 of the present invention.
具体实施方式DETAILED DESCRIPTION
为使本发明实施例的目的、技术方案和优点更加清楚，下面将对本发明实施例中的技术方案进行清楚、完整地描述。实施例中未注明具体条件者，按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者，均为可以通过市售购买获得的常规产品。In order to make the purpose, technical scheme and advantages of the embodiments of the present invention clearer, the technical scheme in the embodiments of the present invention will be described clearly and completely below. If the specific conditions are not specified in the embodiments, they are carried out according to conventional conditions or conditions recommended by the manufacturer. If the manufacturer of the reagents or instruments used is not specified, they are all conventional products that can be purchased commercially.
实施例1:2-硝基-5-氟苯甲醚的制备Example 1: Preparation of 2-nitro-5-fluoroanisole
反应釜中依次加入126mg 3-氟苯甲醚、410mg九水硝酸铁，然后加入1mL六氟异丙醇，控温40-80℃，控温反应6-24h，反应完全后；旋干六氟异丙醇，加入乙酸乙酯萃取3次，弃掉水相，有机相饱和食盐水洗涤，无水硫酸镁干燥，过滤，减压蒸除溶剂即得油状液体产物，柱色谱分离得目标产物110mg,收率64％。126 mg 3-fluoroanisole and 410 mg ferric nitrate nonahydrate were added to the reaction kettle in sequence, and then 1 mL hexafluoroisopropanol was added, and the temperature was controlled at 40-80°C. The temperature was controlled to react for 6-24 hours. After the reaction was complete, the hexafluoroisopropanol was spin-dried, and ethyl acetate was added to extract 3 times. The aqueous phase was discarded, and the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain an oily liquid product. 110 mg of the target product was separated by column chromatography, and the yield was 64%.
实施例2:2-硝基-5-氟苯甲醚的制备Example 2: Preparation of 2-nitro-5-fluoroanisole
反应釜中依次加入126g 3-氟苯甲醚、510g四甲基硝酸铵，然后加入1L六氟异丙醇，控温60℃，控温反应12h，反应完全后；减压蒸馏回收溶剂，加入乙酸乙酯萃取3次，弃掉水相，有机相饱和食盐水洗涤，无水硫酸镁干燥，过滤，减压蒸除溶剂即得油状液体产物，重结晶得目标产物98g,收率57％。126 g 3-fluoroanisole and 510 g tetramethylammonium nitrate were added to the reactor in sequence, and then 1 L hexafluoroisopropanol was added. The temperature was controlled at 60° C. and the reaction was carried out for 12 h. After the reaction was complete, the solvent was recovered by distillation under reduced pressure, ethyl acetate was added for extraction 3 times, the aqueous phase was discarded, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain an oily liquid product. 98 g of the target product was obtained by recrystallization with a yield of 57%.
1H NMR(400MHz,CDCl3)δ7.96(dd,J＝9.0,6.0Hz,1H),6.87-6.67(m,2H),3.97(s,3H). 1 H NMR (400MHz, CDCl 3 ) δ7.96 (dd, J=9.0, 6.0Hz, 1H), 6.87-6.67 (m, 2H), 3.97 (s, 3H).
以上仅为本发明的优选实施例而已，并不用于限制本发明，对于本领域的技术人员来说，本发明可以有各种更改和变化。凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。The above are only preferred embodiments of the present invention and are not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.
Claims (7)
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