Benzyl Bromide → HCID 67486773, compound

Participants

Reaction Steps

To a solution of methyl 3,5-dihydroxybenzoate (50 g, 297 mmol) in DMF (270 ml) is added under nitrogen K2CO3 (61.6 g, 446 mmol, 1.5 eq.). Then benzyl bromide (53 ml, 446 mmol, 1.5 eq.) is added dropwise at 0° C. and the reaction mixture is stirred at RT for 24 h. The reaction mixture is filtered over celite, DMF is evaporated, water (500 ml) added and the reaction mixture extracted with ethyl acetate (2×500 ml). The combined organic layer is washed with brine, dried over MgSO4 and the solvent removed in vacuo. The residue is purified by column chromatography (cyclohexane/ethyl acetate 100/00 to 95/05) to give a mixture of the desired product and the di-alkylated compound. This mixture is purified by column chromatography (cyclohexane/acetone 95/05 to 90/10) to give 17.7 g of the title compound as white powder (yield of 23%).

Provenance & Evidence