Acetanilide → 2-Fluoro-N-phenylacetamide

反応式

[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]

参加物

反応物 5

HCID 904Acetanilide

HCID 9601N-(4-fluorophenyl)acetamide

HCID 78989Hypofluorous acid, trifluoromethyl ester

HCID 96093Acetamide, N-(2,4-difluorophenyl)-

HCID 138072N-(2,6-difluorophenyl)acetamide

生成物 1

HCID 95042-Fluoro-N-phenylacetamide収率 37%

試薬・触媒・溶媒 1

実験手順

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.