Methanol → 1-[(2-Bromoethyl)sulfanyl]-3-fluorobenzene

Participants

Reaction Steps

To 2 mL of a methanol solution containing 0.83 g of 28% sodium methoxide/methanol, 1.0 mL of 1,2-dibromoethane and 0.50 g of 3-fluorobenzenethiol were added under cooling with ice, the mixture was stirred at the same temperature for 1 hour, at room temperature for 2 hours, and at 50° C. for 1 hour, and then the reaction mixture was refluxed by heating for 5 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane] to obtain 0.62 g of a pale yellow oily substance, 1-(3-fluorophenyl)thio-2-bromoethane.

Provenance & Evidence