Sodium Hydroxide → 3-(3-Bromophenyl)propan-1-ol

Temperature

0 °C

A suspension of 1.84 g (8 mmol) of 3-(3-bromophenyl)propionic acid and 0.91 g (24 mmol) of sodium borohydride in 20 ml of THF, cooled to 0° C., is admixed in small portions with 3.2 ml (25 mmol) of trifluoroborane-diethyl ether complex. Stirring is continued in the cold for 1 hour, and then at ambient temperature for 16 hours. The reaction mixture is cooled to 0° C. and neutralized to a pH of 7˜8 by adding a 1N solution of aqueous sodium hydroxide. It is concentrated under reduced pressure and then the residue is taken up in water. It is extracted with dichloromethane and dried over sodium sulphate. Following filtration, the organic phase is concentrated under reduced pressure. This gives 1.62 g (7.53 mmol) of product in the form of an oil, which is used as it is in the following step.

1. customcold for 1 hour
2. temperatureThe reaction mixture is cooled to 0° C. and neutralized to a pH of 7˜8
3. concentrationIt is concentrated under reduced pressure
4. extractionIt is extracted with dichloromethane
5. dry with materialdried over sodium sulphate
6. filtrationfiltration
7. concentrationthe organic phase is concentrated under reduced pressure

ORD record

ord-beb07457d4e8475cbdb04a25541f093e

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482346B2