75-45-6

69519-09-1

43141-66-8

Anhydrous K2CO3 (powder, 4.0 eq.), hydroquinone (2.0 eq.), Pd2(dba)3 (2.5 mol%), Xantphos (7.5 mol%), and aryl borate (ArB(OH)2, 0.3 or 0.5 mmol) or aryl borate (Ar-Beg, 0.3 or 0.5 mmol ), the operation was carried out under argon protection. This was followed by the addition of a solution of chlorodifluoromethane (ClCF2H) in 1,4-dioxane (2.0 M, for the 0.3 mmol scale use 1.5 mL, for the 0.5 mmol scale use 2.5 mL, 10 equivalents) and freshly distilled 1,4-dioxane (for the 0.3 mmol scale use 1.0 mL, for the 0.5 mmol scale use 2.5 mL ). The reaction tube was sealed and heated in an oil bath at 110°C. The reaction mixture was reacted with stirring for 48 h. After cooling to room temperature, fluorobenzene (1.0 equiv) was added. The reaction yield was determined by 19F NMR. The reaction mixture was diluted with ethyl acetate, filtered through a pad of diatomaceous earth and the filtrate was concentrated. The residue was purified by silica gel column chromatography to afford the target product 1-chloro-4-(difluoromethyl)benzene.