Borane;tetrahydrofuran → 2-Bromo-5-(trifluoromethyl)benzyl alcohol

To an ice-cooled solution of 2-bromo-5-(trifluoromethyl)benzoic acid (5.16 g, 19 mmol) in THF (50 mL) was added borane-tetrahydrofuran complex (70 mL of 1M solution in THF, 70 mmol). The resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with methanol. Solvent was removed. The residue was partitioned between ethyl acetate (3×40 mL) and 1M sodium bicarbonate (50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4) and concentrated to yield the title compound as an oil (4.85 g). 1H NMR (400 MHz, CDCl3) δ 4.8 (s, 2 H) 7.5 (m, 1 H) 7.7 (d, J=8.2 Hz, 1 H) 7.8 (d, J=1.6 Hz, 1 H).

1. customThe reaction mixture was quenched with methanol
2. customSolvent was removed
3. customThe residue was partitioned between ethyl acetate (3×40 mL) and 1M sodium bicarbonate (50 mL)
4. washThe combined organic layers were washed with saturated NaCl (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated

ORD record

ord-0ba15b80095a49f089ecf99eacfd814e

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383660B2