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

HRID 705865Notes

Reaction equation

HRID 705865 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

4

Reactant 2

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

Product 1

HCID 668254365-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrileYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-formyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (1 g, 3.43 mmol) and NaBH4 (0.156 g, 4.12 mmol) in ethanol (20 mL) was stirred at room temperature for 3 h. The reaction was quenched with NH4Cl saturated solution and extracted with EA. The organic layer was separated and concentrated to afford the title compound (0.9 g, 89% yield) as a white solid. LCMS: rt=3.71 min

Workup

  1. customThe reaction was quenched with NH4Cl saturated solution
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-daa31dd830be488caa0b9496f3650b41
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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