Nitrogen → 3-(2-Bromophenyl)propan-1-ol

3-(2-Bromophenyl)propionic acid (1.15 g, 5.0 mmol) was placed in a 100 mL three-necked flask with magnetic stirrer. The atmosphere was exchanged with N2 (3 times). With ice cooling, a solution of BH3.THF in THF (1.0M, 7.0 mL, 1.4 equiv.) was added dropwise via syringe with stirring over a 15 min period (H2 evolution). The resulting mixture was stirred in the ice bath for 1 h, and residual borane was quenched by cautious addition of water. The solvents were evaporated, and the residue was partitioned between ether (20 mL) and water (20 mL). The aqueous phase was extracted with ether (20 mL). The combined ether layers were washed with brine, dried over Na2SO4, and concentrated to give the alcohol as a clear oil (1.05 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 7.53 (d, 1H, J=7.8 Hz), 7.26-7.22 (m, 2H), 7.09-7.03 (m, 1H), 3.71 (t, 2H, J=6.4 Hz), 2.87-2.82 (m, 2H), 1.94-1.86 (m, 2H), 1.36 (br s, 1H).

1. customresidual borane was quenched by cautious addition of water
2. customThe solvents were evaporated
3. customthe residue was partitioned between ether (20 mL) and water (20 mL)
4. extractionThe aqueous phase was extracted with ether (20 mL)
5. washThe combined ether layers were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated

ORD record

ord-ecf42cc3afd349ec924eca958ad52b1f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445684B2