(Dimethyl sulfide)trihydroboron → 2-[2-(4-Bromophenyl)ethoxy]ethanol

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%).

1. temperatureAfter cooling the reaction mixture to between 0 and 5° C.
2. addition1.5 NHCl (80 mL) was added
3. temperaturedropwise, and the resulting mixture was refluxed for 30 minutes
4. temperatureThe reaction mixture was cooled to room temperature
5. extractionextracted with ethyl acetate (2×100 mL)
6. washThe combined organic layers were washed with water and brine
7. concentrationconcentrated

ORD record

ord-198a46ae7f114510a733a320a69456d1

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928225B2