Acetic acid, 2-chloro-2,2-difluoro-, ethyl ester → 2-Chloro-1-methyl-4-(trifluoromethyl)benzene

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-iodotoluene (22.0 g) was dissolved in N,N-dimethylformamide (110 ml), and copper(I) iodide (49.8 g), ethyl chlorodifluoroacetate (37.8 g) and potassium fluoride (15.2 g) were added. The mixture was stirred at internal temperature of 116° C. for 70 hr. The reaction mixture was filtered through celite. Water (11 ml) and diethyl ether (110 ml) were added to the filtrate under ice-cooling and the mixture was filtered through celite. The filtrate was separated and the aqueous layer was extracted again with diethyl ether (110 ml). The organic layers were combined and washed with saturated brine (110 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2-chloro-4-trifluoromethyltoluene (23.0 g) as a brown oil.

Provenance & Evidence