Benzyl Bromide → 2-(Benzyloxy)-1,3-dibromobenzene

Participants

Reaction Conditions

Reaction Steps

Powdered K2CO3 (27.6 g, 200 mmol, 2.0 equiv) was added to a solution of 2,6-dibromophenol (14) (25.0 g, 100 mmol, 1.0 equiv) in MeCN (300 mL). Benzyl bromide (18.0 g, 12.5 mL, 105 mmol, 1.05 equiv) was added slowly to the light blue suspension. The reaction temperature increased only from 22 to 24° C. over 5 min. The reaction suspension was heated at reflux for 6 hr, allowed to cool to room temperature and stand for 48 hr. The mixture was filtered, solids were washed with EtOAc (300 mL) and the filtrate was concentrated under reduced pressure. The residual oil was dissolved in 1:1 MTBE/heptanes (500 mL), the solution washed with 10% NaOH (100 mL), H2O (100 mL), brine (100 mL), dried over Na2SO4, filtered and the solution concentrated under reduced pressure giving 36.9 g (108%) of crude 15 as a yellow oil that crystallized after pumping on high vacuum for 1.5 hr. Crude 15 was used without further purification.

Provenance & Evidence