1,1-Dichloroethane → Chloromethyl 3-fluorobenzoate

To 10 ml of dichloroethane were added 1.32 g of zirconium tetrachloride and 1 g of 3-fluorobenzoyl chloride, and the mixture was stirred at room temperature for 20 minutes. The mixture was cooled to 0° C., 0.21 g of trioxane was added, and the mixture was stirred for 1 hour, and further stirred at room temperature for 1 hour. Water was added slowly at 0° C., the resultant solution was extracted with chloroform three times, and the organic layers were combined, washed with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated to obtain 0.65 g of chloromethyl 3-fluorobenzoate.