methyl 4-bromo-2-(2-methylpropyl)benzoate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-2-fluorobenzoic acid (2.0 g) in tetrahydrofran (15 ml) was added 2M isobutylmagnesium bromide in diethyl ether (13.5 ml) dropwise on ice-cooling, and the mixture was stirred at 0° C. for 1 hour. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. To the solution of the residue in N,N-dimethylformamide (20 ml) was added methyliodide (1.14 g) and potassium carbonate (1.89 g), and the mixture was stirred at 20° C. for 3 hours. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give methyl 4-bromo-2-isobutylbenzoate (1.5 g) as a colorless oil. cooling The organic layer was separated washed with brine dried over magnesium sulfate evaporated To the solution of the residue in N,N-dimethylformamide (20 ml) was added methyliodide (1.14 g) and potassium carbonate (1.89 g) the mixture was stirred at 20° C. for 3 hours The mixture was diluted with ethyl acetate and water The organic layer was separated washed with brine dried over magnesium sulfate evaporated The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-2-fluorobenzoic acid (2.0 g) in tetrahydrofran (15 ml) was added 2M isobutylmagnesium bromide in diethyl ether (13.5 ml) dropwise on ice-cooling, and the mixture was stirred at 0° C. for 1 hour. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. To the solution of the residue in N,N-dimethylformamide (20 ml) was added methyliodide (1.14 g) and potassium carbonate (1.89 g), and the mixture was stirred at 20° C. for 3 hours. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give methyl 4-bromo-2-isobutylbenzoate (1.5 g) as a colorless oil. cooling The organic layer was separated washed with brine dried over magnesium sulfate evaporated To the solution of the residue in N,N-dimethylformamide (20 ml) was added methyliodide (1.14 g) and potassium carbonate (1.89 g) the mixture was stirred at 20° C. for 3 hours The mixture was diluted with ethyl acetate and water The organic layer was separated washed with brine dried over magnesium sulfate evaporated The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)