4'-Bromo-4-(dimethylamino)biphenyl-2-carboxylic acid → (4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17](O)=[O:18])=[CH:10][C:11]([N:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:15])[CH3:16])=[CH:10][C:9]=2[CH2:17][OH:18])=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
4′-bromo-4-(dimethylamino)biphenyl-2-carboxylic acid (1.34 g, 4.19 mmol) in THF (40 mL) was cooled to 0° C. Borane tetrahydrofuran complex (8.37 mL, 8.37 mmol) was added dropwise over 15 min. and allowed to warm up to r.t. overnight. The reaction was diluted with EtOAc and washed with water, saturated ammonium chloride, and then brine. The organic layer was dried over MgSO4, filtered and evaporated to give (4′-bromo-4-(dimethylamino)biphenyl-2-yl)methanol (1.25 g, 4.08 mmol, 98% yield) as a white solid. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 2.93-3.05 (m, 6H) 4.58 (s, 2H) 6.72 (dd, J=8.55, 2.75 Hz, 1H) 6.90 (d, J=2.75 Hz, 1H) 7.14 (d, J=8.55 Hz, 1H) 7.21-7.25 (m, 2H) 7.44-7.55 (m, 2H).