Benzeneacetic acid, 4-bromo- → 2-(4-Bromophenyl)ethanol

To a chilled solution (about 0° C.) of 4-bromophenyl acetic acid (25 g, 0.116 mol) in THF (250 mL), borane methyl sulphide (13.2 g, 0.174 mol) was added, dropwise, under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 h. After cooling the mixture to between 0 and 5° C., the reaction was quenched by adding 1.5 N HCl (80 mL), dropwise. After warming for 30 min at about 80° C., the reaction mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water and brine and then dried. The product was obtained as colourless liquid after concentration (yield: 23.3 g, 99%).

1. temperatureAfter cooling the mixture to between 0 and 5° C.
2. customthe reaction was quenched
3. additionby adding 1.5 N HCl (80 mL)
4. temperatureAfter warming for 30 min at about 80° C.
5. extractionthe reaction mixture was extracted with ethyl acetate (2×100 mL)
6. washThe combined organic extracts were washed with water and brine
7. customdried
8. customThe product was obtained as colourless liquid
9. concentrationafter concentration (yield: 23.3 g, 99%)

ORD record

ord-8a1c7e22e9894aeba7c700ded5645eaa

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928225B2