Potassium Carbonate → 2-Bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzene

Participants

Reaction Steps

To a mixture of 0.59 g of 2-bromo-4-(4-chlorophenylthio)phenol, 0.28 g of potassium carbonate and 20 ml of N,N-dimethylformamide, a solution prepared by dissolving 0.30 g of 1,1,3-trichloropropene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After the mixture was stirred at room temperature for 6 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel column chromatography to give 0.62 g of 2-bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzene, yield 78%; nD25.0 1.6514.

Provenance & Evidence