Dimethylformamide → 3-Chloro-2-fluoro-5-(trifluoromethyl)benzamide
Reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([F:19])=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9](O)=[O:10].C[N:21](C)C=O>>[Cl:5][C:6]1[C:7]([F:19])=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9]([NH2:21])=[O:10]Participants
4
Conditions
- Temperature
- 75 °C
Procedure
Thionyl chloride, 6.0 g (50 mmol) was added to a solution of 4.0 g (16 mmol) 3-chloro-2-fluoro-5-(trifluoromethyl) benzoic acid in 10 mL dimethylformamide. The reaction mixture was heated to 75° C. for 2 hours, cooled to room temperature and carefully added to 25 mL of ice cold ammonium hydroxide. The mixture was cooled to 0° C. and the solid product filtered, washed with water and dried to yield 3.96 g (99%) of 3-chloro-2-fluoro-5-(trifluoromethyl)benzamide.