Sodium borohydride → 2,6-Difluoro-4-(hydroxymethyl)benzonitrile
Reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2,6-Difluoro-4-formylbenzonitrile (1.36 g, 8.13 mmol; see step (ii) above) was dissolved in 25 mL of methanol and cooled on an ice bath. Sodium borohydride (0.307 g, 8.12 mmol) was added in portions with stirring and the reaction was left for 65 min. The solvent was evaporated and the residue was partitioned between diethyl ether and aqueous sodium bicarbonate. The ethereal layer was washed with more aqueous sodium bicarbonate and brine, dried (Na2SO4) and evaporated. The crude product crystallised soon and could be used without further purification. Yield: 1.24 g (90%).