Calcium Carbonate → HCID 86694928, compound

Participants

Reaction Steps

To a suspension 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)/water (5 ml) was added calcium carbonate (0.68 g, 6.74 mmol). The mixture was heated in a microwave for 3.5 hours, cooled and the solvent removed in vacuo. The intermediate was suspended in N,N-dimethylformamide (10 ml) and potassium carbonate (0.78 g, 5.62 mmol) and 4-fluorobenzyl bromide (0.61 ml, 4.94 mmol) were added and the mixture stirred for overnight. The solvent was removed in vacuo and the residue taken up in ethyl acetate/H2O (10 ml/10 ml). The organic layer was dried and the solvent removed in vacuo. The residue was redissolved in N,N-dimethylformamide (3 ml) and potassium carbonate (0.78 g, 5.62 mmol) and 4-fluorobenzyl bromide (0.61 ml, 4.94 mmol) added and stirred for 2 hours. Ethyl acetate (20 ml) and water (10 ml) were added, The organic layer was washed further with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 6:1 cyclohexane/ethyl acetate) yielded the title compound as an oil. 920 mg.

Provenance & Evidence