Reaction #2875

Reaction equation

5-bromo-2-fluoro-benzaldehyde

sodium borohydride

→

title compound

Yield 97.7%

5-Bromo-2-fluoro-benzyl alcohol

Yield 97.7%

Solvents

THF

Conditions

Workup

1. 1
   Otherquenched by the addition of 1N HCl
2. 2
   workup.ADDITIONThe mixture is diluted with EtOAc
3. 3
   Otherthe layers are separated
4. 4
   WashThe organic layer is washed with H2O and saturated NaCl
5. 5
   DryingThe organic layer is dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe crude product is purified by column chromatography
9. 9
   Washeluting with 15% EtOAc/hexanes

Procedure

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).

Source