Sodium borohydride → HCID 21099499, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-[(2-bromophenyl)thio]benzaldehyde (Step 1, 5 g, 12.7 mmol) in ethanol under nitrogen (63 mL) was added sodium borohydride (5.7 g, 127.2 mmol). The reaction was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to yield {4-[(2-bromophenyl)thio]phenyl}methanol as a colourless oil (5.0 g, 99%). δH (400 MHz, d6 DMSO): 7.65–7.60 (1H, m), 7.41 (4H, s), 7.27–7.21 (1H, m), 7.14–7.08 (1H, m), 6.83 (1H, dd, J=1.4, 7.9 Hz), 5.32–5.28 (1H, m), 4.56–4.53 (2H, m).