Carbon tetrabromide → Methyl 2-(4-fluorophenethyl)-5-bromomethylbenzoate

Participants

Reaction Steps

A mixture of methyl 2-(4-fluorophenethyl)-5-hydroxymethylbenzoate (13.10 g., 45.43 mmol), carbon tetrabromide(18.08 g, 54.52 mmol) and triphenylphosphine (14.30 g, 54.52 mmol) in dichloromethane (400 ml) was stirred at ambient temperature for 4 hours. More carbon tetrabromide (7.54 g, 23.00 mmol) and triphenylphosphine (5.96 g, 23.00 mmo.) in dichloromethane (50 ml) were added. The reaction was applied directly to a silica flash column and eluted with iso-hexane/ethyl acetate (92.5:7.5) to give methyl 2-(4-fluorophenethyl)-5-bromomethylbenzoate (9.30 g) as a clear gum.

Provenance & Evidence