Carbon tetrabromide → Benzyl 3-[4-(bromomethyl)phenyl]propyl ether

Participants

Reaction Conditions

Reaction Steps

{4-[3-(benzyloxy)propyl]benzyl alcohol (1.86 g, 7.31 mmol) was dissolved in 82 mL dichloromethane. The solution was cooled to 0° C. 3.25 g (12.41 mmol) triphenyl phosphine and 4.11 g (12.41 mmol) carbon tetrabromide were added to the solution. The ice bath was removed and the reaction was stirred for 1 h. The solution was concentrated in vacuo, to the residue was added tert-butyl methyl ether (100 mL) and the mixture was stirred at −20° C. for 30 min. The mixture was filtrated and the filtrate was concentrated in vacuo. The crude product was purified on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Provenance & Evidence