3-bromo-2,4-dimethylbenzoic acid → (3-Bromo-2,4-dimethylphenyl)methanol
Reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[CH3:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Bromo-2,4-dimethylbenzoic acid (6.50 g, 28.4 mmol), in THF (50 mL) was treated with borane tetrahydrofuran complex (42.6 mL, 42.6 mmol) and stirred for 12 h. Analysis by LC indicated that reaction had gone to completion. The solution was concentrated to dryness, redissolved in DCM, and washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The resulting (3-bromo-2,4-dimethylphenyl)methanol was used for the next step with out further purification. 1H-NMR (CDCl3, 500 MHz), δ 7.227 (d, J=7.5 Hz, 1H), 7.122 (d, J=7.5 Hz, 1H), 4.730 (m, 2H), 2.492 (s, 3H), 2.456 (s, 3H).