Monobenzone → 2-Bromo-4-(phenylmethoxy)phenol

Participants

Reaction Steps

To a suspension of 4-benzyloxyphenol (30 g, 150 mmol) in chloroform (400 ml) was added, dropwise, a solution of bromine (24 g, 150 mmol) in chloroform (150 ml). After stirring for 1 hour the mixture was washed with 0.1M NaHSO3 (500 ml), then water (500 ml). The chloroform layer was separated, dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 5, 10, 20% ethyl acetate/hexane. Recrystallisation from hexane afforded the title compound (20.5 g, 49%); δH (250MHz, CDCl3) 4.98 (2H, s, OCH2), 6.82--6.99 (2H, m, ArH), 7.09-7.12 (1H, d, J 2.75Hz, ArH), 7.30-7.42 (5H, m).

Provenance & Evidence