Benzyl Bromide → HCID 86694931, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-(acetyloxy)-5-chloro-4-(dibromomethyl)benzoate (may be prepared as described in Description 61; 2.1 g, 5.24 mmol) and calcium carbonate (1.05 g, 10.49 mmol) in 1,4-dioxane (5 ml)/water (5 ml) was heated at 150° C. for 6 hours. The solvent was removed in vacuo and the residue was suspended in N,N-dimethylformamide (5 ml). Cesium carbonate (3.76 g, 11.54 mmol) and benzyl bromide (0.94 ml, 7.87 mmol) were added. The mixture was heated at 50° C. for 18 hours. The N,N-dimethylformamide was removed and the residue was partitioned between 2M HCl (20 ml) and ethyl acetate (15 ml). The organic layer was separated and dried (MgSO4) and the solvent removed in vacuo. The residue was redissolved in N,N-dimethylformamide (5 ml) and cesium carbonate (3.76 g, 11.54 mmol) and benzyl bromide (0.94 ml, 7.87 mmol) were added. The mixture was heated for 2 hours at 50° C. and cooled, then ethyl acetate (15 ml) and water (10 ml) were added. The organic layer was washed with water (2×15 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (6:1 cyclohexane/ethyl acetate) gave the title compound as an off white solid. 1.4 g.

Provenance & Evidence