Phosphorus tribromide → 1-(Benzyloxy)-2-(bromomethyl)-4-chlorobenzene

Participants

Reaction Conditions

Reaction Steps

{5-chloro-2-[(phenylmethyl)oxy]phenyl}methanol (8.2 g, 33 mmol) was dissolved in dry dichloromethane under nitrogen and cooled to −10° C. Phosphorus tribromide (3.12 ml, 33 mmol) in dry dichloromethane (15 ml) was added slowly. The mixture was left at −10° C. for 15 mins, then stirred at room temperature overnight. TLC showed no more starting material. The mixture was then quenched with a saturated sodium hydrogen carbonate solution added very slowly. The mixture was diluted with dichloromethane and brine was added to aid separation. The organic phase was washed with water (×2), then dried (MgSO4) and evaporated. The residue was purified (50 g SPE column). Product comes off using 5% ethyl acetate in isohexane. White-ish solid obtained (8.1 g).

Provenance & Evidence