Benzyl Bromide → HCID 86694927, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(acetyloxy)-5-bromo-4-(dibromomethyl)benzoate (may be prepared as described in Description 23; 1 g, 2.25 mmol) in 1,4-dioxane (5 ml) was added calcium carbonate (0.68 g, 6.74 mmol) and water (5 ml). The mixture was heated at 150° C. for 3 hours, cooled and the solvent was removed in vacuo. The residue was suspended in N,N-dimethylformamide (5 ml) and potassium carbonate (0.78 g, 5.62 mmol) and benzyl bromide (0.59 ml, 4.94 mmol) were added and the mixture was stirred for 18 hours. Ethyl acetate (15 ml) and water (10 ml) were added and the organic layer washed further with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Some starting material was still present. The residue was redissolved in N,N-dimethylformamide (5 ml) and potassium carbonate (0.78 g, 5.62 mmol) and benzyl bromide (0.59 ml, 4.94 mmol) were added and heated at 50° C. for 3 hours, cooled and the solvent was removed in vacuo. Purification by column chromatography (SiO2; 6:1 cyclohexane/ethyl acetate) yielded the title compound as an oil. 956 mg.

Provenance & Evidence