Phenol → 1-Bromo-2-chloro-4-(1-phenoxyethyl)benzene

Participants

Reaction Steps

A solution of 1-(4-bromo-3-chlorophenyl)ethanol (1.32 g, 5.6 mmol), phenol (525 mg, 5.6 mmol) and triphenylphosphine (2198 mg, 8.4 mmol) in tetrahydrofuran (30 mL) was stirred at room temperature for 0.5 hour. Diisopropyl azodicarboxylate (1695 mg, 8.4 mmol) was dropwise to the reaction mixture and was stirred at room temperature for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1) to give 1-bromo-2-chloro-4-(1-phenoxyethyl)benzene as a colorless oil (882 mg 54%). 1H NMR (300 MHz, CDCl3): 7.37 (d, J=8.1, 1H), 7.27-7.20 (m, 4H), 6.92-6.82 (m, 3H), 5.30 (q, J=6.6, 1H), 1.62 (d, J=6.6, 3H).

Provenance & Evidence