Sodium borohydride → 3,5-Difluoro-4-(hydroxymethyl)benzonitrile
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[CH:10]=[O:11])[C:5]#[N:6].[BH4-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[CH2:10][OH:11])[C:5]#[N:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3,5-difluoro-4-formylbenzonitrile (1.0 g, 6.0 mmol) in EtOH (15 mL) at 0° C. was added NaBH4 (113 mg, 0.5 equiv). After stirring 2 h at 0° C., the reaction mixture was quenched with water and concentrated under reduced pressure. The crude residue was dissolved in DCM, washed with brine, dried over Na2SO4 and concentrated to give 3,5-difluoro-4-(hydroxymethyl)benzonitrile as a solid. All material was used in the next step. 1H NMR (400 MHz, CDCl3) δ 7.29-7.15 (m, 2H), 4.82 (d, J=6.2, 2H), 2.02 (dd, J=12.0, 5.6, 1H); GC-MS (ES) m/z 169 (M).