(Diethylamino)sulfur trifluoride → 1-Bromo-4-chloro-3-fluoromethyl-2-fluorobenzene

Participants

Reaction Steps

A solution of diethylamino sulfur trifluoride (7.6 g, 0.047 mol) in methylene chloride (25 mL) was slowly added to (3-bromo-6-chloro-2-fluorophenyl) methanol (10.3 g, 0.043 mol) in methylene chloride (150 mL) at 0° C. The solution was stirred at ambient temperature for 1 hour. A saturated solution of sodium bicarbonate (100 mL) was cautiously added and the mixture extracted with methylene chloride (2×100 mL). The combined organic phases were dried (sodium sulfate) and concentrated. The dark residual oil was purified by chromatography (5% ethyl acetate in hexanes) to give 1-bromo-4-chloro-3-fluoromethyl-2-fluorobenzene (6.20 g, 0.024 mol): 1H NMR (CDCl3): δ 7.55(m, 1H) 7.18 (dd, 1H) 5.6 (d, 2H).

Provenance & Evidence