Methyl 4-bromo-3-methylbenzoate → (4-Bromo-3-methylphenyl)methanol

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A solution of methyl-4-bromo-3-methylbenzoate (4.31 g) in dry tetrahydrofuran (20 ml) was stirred and cooled to 0° C. under nitrogen gas. A solution of 1.5M diisobutylaluminium hydride in toluene (44 ml) was added slowly and the reaction stirred for 2.5 hours, then quenched with methanol and allowed to warm to 21° C. Silica was added and the reaction concentrated in vacuo and purified using SPE (Si cartridge) using cyclohexane:ethyl acetate (3:1) as an eluent which furnished the title compound as a brown oil.

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