Hydrochloric Acid → HCID 69102536, compound

Participants

Reaction Steps

To a mixture of magnesium (1.61 g) in tetrahydrofuran (10 ml) was added a solution of isoamyl bromide (5.0 g) in tetrahydrofuran (23 ml) dropwise at room temperature under nitrogen, and the mixture was refluxed for 0.5 hour and cooled to room temperature. The mixture was transferred via a syringe to a solution of 4-bromo-2-fluorobenzoic acid (2.5 g) in tetrahydrofuran (15 ml) at 4-10° C. The resulting mixture was stirred at room temperature for 16 hours. To the reaction mixture was added water (200 ml) dropwise with ice-cooling. The aqueous solution was acidified with 6N aqueous hydrochloride solution and extracted with ethyl acetate (150 ml×2). The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform/methanol=10/1) to give 4-bromo-2-(3-methylbutyl)benzoic acid (1.35 g).

Provenance & Evidence