Benzyl Chloride → 1-Bromo-4-phenylmethoxybenzene

Participants

Reaction Steps

4-Bromophenol (17.3 g, 0.1 mol), 19.03 g (0.15 mol) benzyl chloride, and 27.64 g (0.2 mol) pulverized K2CO3 were suspended in 150 mL Me2CO and heated to reflux 2 h. The resulting suspension was concentrated on a rotary evaporator. The mixture was then diluted with 200 mL 5% NaOH and extracted with 100 mL Et2O. The organic layer was washed with an additional 100 mL 5% NaOH, dried (MgSO4), filtered, and concentrated to give a yellow oil, which was crystallized and recrystallized from boiling EtOH to yield 17 g (65%) of Benzyl 4-bromo phenyl ether as white needles, mp: 60°-61° C. NMR δ 7.35 and 6.82 (AA'BB', c, 4H, C6H4), 7.36 (s, 5H, C6H5), 5.0 (s, 2H, OCH2).

Provenance & Evidence