Sodium borohydride → 5-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile

HRID 873041Notes

Reaction equation

HRID 873041 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4]>CO>[OH:4][CH2:3][C:5]1[CH:6]=[CH:7][C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[C:9]([CH:12]=1)[C:10]#[N:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666203Benzonitrile, 5-formyl-2-[3-(trifluoromethyl)phenoxy]-

Product 1

HCID 668254365-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrileYield 109.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.39 g, 10.30 mmol) was added to a solution of 5-formyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (5 g, 17.17 mmol) in methanol (30 mL) at 0° C., and then the mixture was stirred at rt for 30 min. The reaction mixture was quenched by acetone and concentrated. The residue was purified via ISCO (DCM:MeOH=20:1) to afford the title compound as a clear oil (5.5 g, 95% yield).

Workup

  1. customThe reaction mixture was quenched by acetone
  2. concentrationconcentrated
  3. customThe residue was purified via ISCO (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-26b27fa5ce5142948af2c2bd3002a9be
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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