3'-Bromoacetophenone → 2-(3-Bromophenyl)propan-2-ol

Participants

Reaction Steps

To a solution of 3.34 g (16.8 mmol) of 3'-bromoacetophenone in dry diethyl ether (68 ml) was added 1.4M diethyl ether solution of methyllithium (18.0 ml, 25.2 mmol) in an atmosphere of argon at 0° C., and the mixture was allowed to react for 30 min. To the solution was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-methanol yielded 3.47 g (16.1 mmol) of 3-(α-hydroxyisopropyl)-1-bromobenzene.

Provenance & Evidence