CN114163346A - Synthesis method of o-bromo-p-fluoroacetanilide - Google Patents
Synthesis method of o-bromo-p-fluoroacetanilide Download PDFInfo
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- CN114163346A CN114163346A CN202111625298.1A CN202111625298A CN114163346A CN 114163346 A CN114163346 A CN 114163346A CN 202111625298 A CN202111625298 A CN 202111625298A CN 114163346 A CN114163346 A CN 114163346A
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- fluoroacetanilide
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- JAVSBNOXENOHEI-UHFFFAOYSA-N n-(2-bromo-4-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1Br JAVSBNOXENOHEI-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000001308 synthesis method Methods 0.000 title description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 8
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 8
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 229940126062 Compound A Drugs 0.000 claims description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000004321 preservation Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 3
- KDLPMPVDTPYPJQ-UHFFFAOYSA-N 1-(4-amino-3-bromophenyl)-2-fluoroethanone Chemical compound NC1=CC=C(C(=O)CF)C=C1Br KDLPMPVDTPYPJQ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005917 acylation reaction Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000005893 bromination reaction Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 238000006722 reduction reaction Methods 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
- 229960001413 acetanilide Drugs 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000002221 antipyretic Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- GDAZZZLHHSQPOQ-UHFFFAOYSA-N 2-methyl-3-phenyloxaziridine Chemical compound CN1OC1C1=CC=CC=C1 GDAZZZLHHSQPOQ-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940085790 synthetic camphor Drugs 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
- C07C209/365—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst by reduction with preservation of halogen-atoms in compounds containing nitro groups and halogen atoms bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for synthesizing o-bromo-p-fluoroacetanilide, belonging to the technical field of chemical intermediate synthesis. The method takes potassium fluoride and p-chloronitrobenzene as starting materials, and prepares the o-bromo-p-fluoroacetylaniline through halogen exchange, reduction, acylation reaction and bromination reaction.
Description
Technical Field
The invention relates to a method for synthesizing o-bromo-p-fluoroacetanilide, belonging to the technical field of chemical intermediate synthesis.
Background
Acetanilide is an organic compound with a chemical formula of C8H9NO, is colorless and glittering lobular solid or white crystalline powder, is a raw material of sulfonamides, and can be used as an analgesic, an antipyretic, a preservative and a dye intermediate.
Acetanilide is a raw material of sulfonamides and can be used as an analgesic, antipyretic and preservative. Used for manufacturing dye intermediates of paranitroacetanilide, paranitroaniline and p-phenylenediamine. Acetanilide is also used in the production of thioacetamide. Can be used as rubber vulcanization accelerator, stabilizer for fiber grease coating, stabilizer for hydrogen peroxide, and synthetic camphor. It is also used as a medium for preparing penicillin G. The former generation of analgesic and antipyretic drugs have been replaced by the new generation of acetyl drugs because of their low toxicity.
O-bromo-p-fluoroacetanilide is a derivative of acetanilide and has an excellent application prospect, but no synthesis method for the derivative exists at present, and a synthesis method for o-bromo-p-fluoroacetanilide is urgently needed.
Disclosure of Invention
A synthetic method of o-bromo-p-fluoroacetanilide comprises the following steps:
(1) adding DMF, potassium fluoride, p-chloronitrobenzene and PEG400 into a reaction kettle, heating to 210-215 ℃, carrying out heat preservation reaction, and carrying out reduced pressure distillation to obtain a compound A
(2) Adding methanol into a reaction kettle, adding 5% palladium-carbon catalyst, adding a compound A, performing nitrogen replacement and hydrogen replacement, pressurizing by using hydrogen, controlling the temperature to be 50-60 ℃, reacting, cooling, filtering and concentrating to obtain a compound B
(3) Adding dichloromethane into a reaction kettle, adding a compound B, dropwise adding acetic anhydride, controlling the temperature to be 25-30 ℃, and carrying out heat preservation reaction after dropwise adding is finished to obtain a compound C
(4) And (3) putting the compound C into a reactor, cooling to 10-15 ℃, dropwise adding bromine, keeping the temperature for reaction after dropwise adding, adding water, stirring, standing for layering, washing an organic layer with a sodium bisulfite aqueous solution, standing, layering, concentrating, adding methanol, heating for dissolving, cooling to 0-5 ℃, crystallizing, filtering, centrifuging, and drying to obtain the o-bromo-p-fluoroacetanilide.
In the step (1), the mass ratio of DMF, potassium fluoride, p-chloronitrobenzene and PEG400 is 15: 2-5: 4: 0.1.
The mass ratio of the methanol to the 5% palladium-carbon catalyst to the compound A in the step (2) is 8:0.05: 2-4
In the step (3), the mass ratio of the dichloromethane to the compound B to the acetic anhydride is 9:3: 2-4
The mass ratio of the compound C, bromine, water and methanol in the step (4) is 16:4:5: 15-17.
Has the advantages that:
the method takes potassium fluoride and p-chloronitrobenzene as starting materials, and prepares the o-bromo-p-fluoroacetylaniline through halogen exchange, reduction, acylation reaction and bromination reaction.
Detailed Description
Example 1
A synthetic method of o-bromo-p-fluoroacetanilide comprises the following steps:
(1) 1500kg of DMF and 200kg of potassium fluoride are added into a reaction kettle, the temperature is raised to 100 ℃, dehydration is carried out for 1h, 400kg of p-chloronitrobenzene is added, and 10kg of PEG400 is added. Heating to 210 ℃, reacting for 5 hours under the condition of heat preservation, and distilling under reduced pressure to obtain 276kg of compound A with the purity of 95.6 percent;
(2) adding 800kg of methanol into a reaction kettle, adding 5kg of 5% palladium-carbon catalyst, adding 200kg of compound A, performing nitrogen replacement and hydrogen replacement, starting aeration at 30 ℃, and performing pressure: 1.0 MPA; slowly raising the temperature in the hydrogen introduction process, controlling the temperature at 50 ℃, reacting for 5 hours, cooling after the reaction is finished, filtering the catalyst (circularly applying), concentrating and recovering methanol to obtain 195kg of a compound B with the purity of 96.3%;
(3) adding 900kg of dichloromethane into a reaction kettle, adding 300kg of compound B, dropwise adding 200kg of acetic anhydride, controlling the temperature to be 25 ℃, and keeping the temperature for reaction for 2 hours after dropwise adding to obtain 1622kg of compound C;
(4) putting 1600kg of compound C into a reactor, cooling to 10-15 ℃, dropwise adding 400kg of bromine, paying attention to tail gas absorption in the dropwise adding process, carrying out heat preservation reaction for 3h after dropwise adding, adding 500kg of water, stirring, standing for layering, washing an organic layer with a sodium bisulfite aqueous solution, standing, layering, concentrating a dichloromethane layer until no fraction is generated, adding 1500kg of methanol, heating for dissolving, cooling to 0-5 ℃, crystallizing for 1h, carrying out suction filtration, centrifuging, and drying to obtain 612kg of o-bromo-p-fluoroacetanilide with the purity of 98.6%.
Nuclear magnetic data: 1H NMR (CDCl 3) 8.27(dd, J =8.8,5.7Hz, 1H), 7.50(s, 1H), 7.29(dd, J =7.8,2.6Hz, 1H), 7.05(td, J =9.1,2.7Hz, 1H), 2.23(s, 3H).
Example 2
A synthetic method of o-bromo-p-fluoroacetanilide comprises the following steps:
(1) 1500kg of DMF and 500kg of potassium fluoride are added into a reaction kettle, the temperature is raised to 100 ℃, dehydration is carried out for 1h, 400kg of p-chloronitrobenzene is added, and 10kg of PEG400 is added. Heating to 210 ℃, reacting for 5 hours while keeping the temperature, and distilling under reduced pressure to obtain 282kg of a compound A with the purity of 96.5 percent; (ii) a
(2) Adding 800kg of methanol into a reaction kettle, adding 5kg of 5% palladium-carbon catalyst, adding 400kg of compound A, performing nitrogen replacement and hydrogen replacement, starting aeration at 30 ℃, and performing pressure: 1.0 MPA; slowly raising the temperature in the hydrogen introduction process, controlling the temperature at 50 ℃, reacting for 5 hours, cooling after the reaction is finished, filtering the catalyst (circularly applying), concentrating and recovering methanol to obtain 201kg of a compound B with the purity of 97.1%;
(3) adding 900kg of dichloromethane into a reaction kettle, adding 300kg of compound B, dropwise adding 400kg of acetic anhydride, controlling the temperature to be 25 ℃, and keeping the temperature for reaction for 2 hours after dropwise adding is finished to obtain 1635kg of compound C;
(4) putting 1600kg of compound C into a reactor, cooling to 10-15 ℃, dropwise adding 400kg of bromine, paying attention to tail gas absorption in the dropwise adding process, carrying out heat preservation reaction for 3h after dropwise adding, adding 500kg of water, stirring, standing for layering, washing an organic layer with a sodium bisulfite aqueous solution, standing, layering, concentrating a dichloromethane layer until no fraction is generated, adding 1700kg of methanol, heating for dissolving, cooling to 0-5 ℃, crystallizing for 1h, carrying out suction filtration, centrifuging, and drying to obtain 633kg of o-bromo-p-fluoroacetanilide with the purity of 98.8%.
Nuclear magnetic data: 1H NMR (CDCl 3) 8.27(dd, J =8.8,5.7Hz, 1H), 7.50(s, 1H), 7.29(dd, J =7.8,2.6Hz, 1H), 7.05(td, J =9.1,2.7Hz, 1H), 2.23(s, 3H).
Claims (5)
1. A synthetic method of o-bromo-p-fluoroacetanilide is characterized by comprising the following steps:
(1) adding DMF, potassium fluoride, p-chloronitrobenzene and PEG400 into a reaction kettle, heating to 210-215 ℃, carrying out heat preservation reaction, and carrying out reduced pressure distillation to obtain a compound A
(2) Adding methanol into a reaction kettle, adding 5% palladium-carbon catalyst, adding a compound A, performing nitrogen replacement and hydrogen replacement, pressurizing by using hydrogen, controlling the temperature to be 50-60 ℃, reacting, cooling, filtering and concentrating to obtain a compound B
(3) Adding dichloromethane into a reaction kettle, adding a compound B, dropwise adding acetic anhydride, controlling the temperature to be 25-30 ℃, and carrying out heat preservation reaction after dropwise adding is finished to obtain a compound C
(4) And (3) putting the compound C into a reactor, cooling to 10-15 ℃, dropwise adding bromine, keeping the temperature for reaction after dropwise adding, adding water, stirring, standing for layering, washing an organic layer with a sodium bisulfite aqueous solution, standing, layering, concentrating, adding methanol, heating for dissolving, cooling to 0-5 ℃, crystallizing, filtering, centrifuging, and drying to obtain the o-bromo-p-fluoroacetanilide.
2. The method for synthesizing o-bromo-p-fluoroacetanilide according to claim 1, wherein the mass ratio of DMF, potassium fluoride, p-chloronitrobenzene, and PEG400 in step (1) is 15:2 to 5:4: 0.1.
3. The method for synthesizing o-bromo-p-fluoroacetanilide according to claim 1, wherein the mass ratio of methanol to the 5% palladium-on-carbon catalyst to the compound A in the step (2) is 8:0.05: 2-4.
4. The method for synthesizing o-bromo-p-fluoroacetanilide according to claim 1, wherein the mass ratio of the dichloromethane, the compound B, and the acetic anhydride in step (3) is 9:3: 2-4.
5. The method for synthesizing o-bromo-p-fluoroacetanilide according to claim 1, wherein the mass ratio of the compound C, the bromine, the water, and the methanol in step (4) is 16:4:5: 15-17.
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