Methanol → (4-Bromo-3-fluorophenyl)methanol

To a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBH4 (3.73 g, 99 mmol) in THF (100 mL) was added MeOH (100 mL) dropwise at 20° C. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in DCM (200 mL) and washed with H2O (60 mL) and brine (60 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a white solid of (4-bromo-3-fluorophenyl)methanol (9.8 g, 47.7 mmol, 97.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.54 (t, J=7.8 Hz, 1H), 7.18 (d, J=9.6 Hz, 1H), 7.06 (d, J=7.2 Hz, 1H), 4.56 (s, 2H); ES-LCMS m/z 188.9 (M−17).

1. customthe solvent was removed in vacuo
2. dissolutionThe residue was dissolved in DCM (200 mL)
3. washwashed with H2O (60 mL) and brine (60 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-5ab40ca17b26475399da1bcc09ff6dea

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937071B2