Sodium borohydride → 2,6-Difluoro-4-(hydroxymethyl)benzonitrile

HRID 1717496Notes

Reaction equation

HRID 1717496 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

HCID 4311764Sodium borohydrideHCID 219046552,6-Difluoro-4-formylbenzonitrile

Product 1

HCID 219046292,6-Difluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 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%).

Workup

  1. temperaturecooled on an ice bath
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between diethyl ether and aqueous sodium bicarbonate
  4. washThe ethereal layer washed with more aqueous sodium bicarbonate and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude product crystallised soon
  8. customcould be used without further purification

Sources & evidence

ORD record
ord-ca6d5b9a8a7443f9a72509dde557fce5
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

Loading…