Sodium borohydride → 3,5-Difluoro-4-(hydroxymethyl)benzonitrile

HRID 1627371Notes

Reaction equation

HRID 1627371 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

HCID 4311764Sodium borohydrideHCID 162182563,5-Difluoro-4-formylbenzonitrile

Product 1

HCID 469414123,5-Difluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. customthe reaction mixture was quenched with water
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude residue was dissolved in DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6578a14702c44cd681d00b49c0ecfacb
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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