[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].B.C1COCC1.C1COCC1.O.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[CH3:11]
15 g (70 mmol) of 3-bromo-4-methylbenzoic acid are placed in 150 ml of anhydrous THF in a round-bottomed flask and under a stream of nitrogen. 84 ml of 1M borane/THF are added dropwise and the reaction medium is stirred overnight at room temperature. A THF/water (50/50) solution is added slowly at 0° C. and the mixture is then poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. 14.4 g (100%) of the expected product are obtained in the form of a yellow oil.
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