Benzyl Bromide → HCID 66868184, compound

Participants

Reaction Steps

2.50 g (62.5 mmol) NaH (60% in oil) were suspended under nitrogen in 70 ml dry THF and a solution of 7.1 g (36.2 mmol) 3-(2,3-dimethoxy-phenyl)-propan-1-ol (J. Org. Chem., 1987, 52, 1072) in 50 ml THF was added dropwise at 18° C. The resulting mixture was stirred for 30 minutes and then a solution of 6.81 g (39.8 mmol) benzylbromide in 30 ml THF was added dropwise and the mixture was stirred over night at 18° C. The reaction was quenched with 10 ml water and the organic solvent was evaporated under reduced pressure. The residue was dissolved in 200 ml of ethyl acetate and the organic layer was washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by column chromatography on silica gel (ethyl acetate/n-hexane 1:40) to afford 8 g (77%) of the desired product as a colorless oil.

Provenance & Evidence