Borane → 2-(2-Bromophenyl)ethan-1-ol

To a cooled to 0° C. solution of 10.0 grams (0.0465 mole) of 2-bromophenylacetic acid in 75 milliliters of dry tetrahydrofuran was added dropwise over a one-half hour period, a solution of 0.070 mole of borane in tetrahydrofuran while the reaction mixture was maintained under a nitrogen atmosphere. After completion of the addition, stirring was continued for one hour at ambient temperature, then cooled and the reaction quenched by adding 100 milliliters of water dropwise to the cooled mixture. Thereafter, the mixture was diluted with 100 milliliters of diethyl ether, sodium chloride was added to the resulting mixture and the organic and aqueous phases were mechanically separated. The organic solution was washed with saturated sodium bicarbonate solution and dried over sodium sulfate to obtain a clear, colorless dried solution. The solution was placed on a rotary evaporator to remove the solvent and to obtain 9.11 grams (98 percent) of the desired 2-(2-bromophenyl)ethanol intermediate as a clear oil. The Rf was 0.5 on silica gel when eluted with one percent methanol in chloroform.

1. additionwas added dropwise over a one-half hour period
2. additionAfter completion of the addition
3. temperaturecooled
4. customthe reaction quenched
5. additionby adding 100 milliliters of water dropwise to the cooled mixture
6. additionThereafter, the mixture was diluted with 100 milliliters of diethyl ether, sodium chloride
7. additionwas added to the resulting mixture
8. customthe organic and aqueous phases were mechanically separated
9. washThe organic solution was washed with saturated sodium bicarbonate solution
10. dry with materialdried over sodium sulfate
11. customto obtain a clear, colorless dried solution
12. customThe solution was placed on a rotary evaporator
13. customto remove the solvent

ORD record

ord-a2a85c46e2ab4289bcd37a7e5e89d786

Source dataset

uspto-grants-1987_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04670443