5-Bromo-2-fluorobenzaldehyde → (5-Bromo-2-fluorophenyl)methanol

Temperature

0 °C

To a solution of 5-bromo-2-fluoro-benzaldehyde (6.10 g, 30.0 mmol) in 30 mL of THF at 0° C. is added 5 mL of sodium borohydride (2.0M solution in triglyme, 10.0 mmol). The reaction mixture is stirred at 0° C. for 25 min and then quenched by the addition of 1N HCl. The mixture is diluted with EtOAc and the layers are separated. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with 15% EtOAc/hexanes to afford the title compound (6.00 g, 29.3 mmol).

1. customquenched by the addition of 1N HCl
2. additionThe mixture is diluted with EtOAc
3. customthe layers are separated
4. washThe organic layer is washed with H2O and saturated NaCl
5. dry with materialThe organic layer is dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product is purified by column chromatography
9. washeluting with 15% EtOAc/hexanes

ORD record

ord-dfa8e518af0e4946b9f86e5f4d0e8666

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05731315