Potassium Carbonate → (4-Fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-hydroxy-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 5; 720 mg, 2.28 mmol) in N,N-dimethylformamide (10 ml) was added potassium carbonate (1102 mg, 7.97 mmol) and 4-fluorobenzyl bromide (0.62 ml, 5.01 mmol). The mixture was heated at 50° C. for 2 hours, cooled and the solvent removed in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate (15 ml). The organic layer was separated, washed further with water (2×5 ml), dried (MgSO4) and the solvent removed in vacuo to give a residue. Purification by column (SiO2, 6:1-1:1 cyclohexane/ethyl acetate) gave the product as a pale yellow oil. 544 mg.

Provenance & Evidence