Water → (3-Bromophenyl)acetaldehyde

Participants

Reaction Steps

A mixture of lead tetraacetate (3.6 g, 8.2 mmol) and trifluoroacetic acid (8.25 mL) at 0° C. is treated dropwise with a solution of 1-bromo-3-vinylbenzene (1.5 g, 8.2 ml) in dichloromethane, allowed to warm to room temperature, stirred for 2 h at room temperature, diluted with dichloromethane, poured into water, stirred vigorously and filtered through a pad of celite. The filtrate is separated. The filtercake is rinsed with additional portions of dichloromethane. The combined organic phases are washed sequentially with water, NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to afford (3-bromophenyl)acetaldehyde.

Provenance & Evidence