Water → 2-(2-Bromophenyl)ethan-1-ol

To a solution of 2-bromophenylacetic acid (3.96 g, 18.42 mmol) in 60 mL of anhydrous THF was added slowly at room temperature 24.0 mL (23.95 mmol) of a 1 M solution BH3/THF. After finishing the addition of BH3/THF, the solution was stirred at room temperature for 1 h and then heated at 100° C. for 2 h. After this time, the solution was cooled to room temperature, and a mixture of THF and water (20 mL) was added. Potassium carbonate was then added, along with 60 mL of ether. The organic layer was separated from the mixture, and this layer was washed with water (60 mL), aqueous NaHCO3 (60 mL), and brine (60 mL) before it was dried over magnesium sulfate, filtered, and concentrated to give the crude product. This crude product was purified by silica gel flash chromatography eluting with hexanes and a 5 to 10% gradient of ethyl acetate to give 3.47 g (94%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.57 (d, 1H, J=7.8 Hz), 7.31-7.21 (m, 2H), 7.14-7.08 (m, 1H), 3.90 (app. t, 2H, J=6.6, 6.9 Hz), 3.05 (app. t, 2H, J=6.6 Hz), 1.51 (bs, 1H). 13C NMR (100 MHz, CDCl3): δ 137.76, 132.95, 131.25, 128.19, 127.44, 124.67, 62.04, 39.30. Anal. Calc'd. for C8H9BrO: C, 47.79; H, 4.51. Found: C, 47.75; H, 4.50.

1. temperatureheated at 100° C. for 2 h
2. temperatureAfter this time, the solution was cooled to room temperature
3. additionwas added
4. customThe organic layer was separated from the mixture
5. washthis layer was washed with water (60 mL), aqueous NaHCO3 (60 mL), and brine (60 mL) before it
6. dry with materialwas dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto give the crude product
10. customThis crude product was purified by silica gel flash chromatography
11. washeluting with hexanes
12. customa 5 to 10% gradient of ethyl acetate to give 3.47 g (94%) as a colorless oil

ORD record

ord-b43a5029b95b4130a9d88cd8ba769890

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562989B2