Acetanilide → 2-Fluoro-N-phenylacetamide

HRID 35392

Reaction equation

HRID 35392 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:11]OC(F)(F)F.CC(NC1C=CC(F)=CC=1)=O.CC(NC1C=CC(F)=CC=1F)=O.CC(NC1C(F)=CC=CC=1F)=O>C(Cl)(Cl)Cl>[F:11][CH2:2][C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3]

Participants

7

Reactant 5

HCID 904AcetanilideHCID 9601N-(4-fluorophenyl)acetamideHCID 78989Hypofluorous acid, trifluoromethyl esterHCID 96093Acetamide, N-(2,4-difluorophenyl)-HCID 138072N-(2,6-difluorophenyl)acetamide

Product 1

HCID 95042-Fluoro-N-phenylacetamideYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 67.5 parts of acetanilide in 22,200 parts of chloroform was cooled to 0° C. and maintained at that temperature for 2.5 hours while fluoroxytrifluoromethane was bubbled into the solution at a rate of 46 parts per hour. Analysis of the reaction product by gas chromatographic technique indicated a 91 percent conversion with a yield of 37% 2-fluoroacetanilide, 16% 4-fluoroacetanilide, 10% 2,4-difluoroacetanilide, 3% 2,6-difluoroacetanilide and about 25% higher molecular weight material.

Workup

  1. customwas bubbled into the solution at a rate of 46 parts per hour

Sources & evidence

ORD record
ord-dd03a1401fc5494786ce532f55efd99a
Source dataset
uspto-grants-1988_08
Patent number
US04766243

Linked notes

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