(Dimethyl sulfide)trihydroboron → 2-[2-(4-Bromophenyl)ethoxy]ethanol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][C:12](O)=[O:13])=[CH:4][CH:3]=1.CSC.B>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of [2-(4-bromophenyl)ethoxy]acetic acid (14 g, 0.054 mol; see step (ii) above) in dry THF (150 mL), borane methyl sulphide (6.16 g, 0.082 mol) was added, dropwise at from 0 to 5° C. The resulting mixture was stirred at room temperature for 3 h. After cooling the reaction mixture to between 0 and 5° C., 1.5 NHCl (80 mL) was added, dropwise, and the resulting mixture was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water and brine and concentrated to give the sub-title compound (yield: 10.8 g, 81%).