Sodium borohydride → 2-{[4-Fluoro-3-(trifluoromethyl)phenyl]oxy}-5-(hydroxymethyl)benzonitrile

HRID 474620Notes

Reaction equation

HRID 474620 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666202Benzonitrile, 2-[4-fluoro-3-(trifluoromethyl)phenoxy]-5-formyl-

Product 1

HCID 668254512-{[4-Fluoro-3-(trifluoromethyl)phenyl]oxy}-5-(hydroxymethyl)benzonitrileYield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}-5-formylbenzonitrile (1.74 g, 5.63 mmol) in ethanol (40 ml), was added NaBH4 (0.255 g, 6.75 mmol). The solution was stirred at room temperature under nitrogen for 1.5 h. After removing the solvent, the residue was dissolved in DCM, then washed with water twice. The solvent was dried over Na2SO4, concentrated to afford the title compound (1.23 g, 70% yield) as a green solid. LCMS: rt=3.06 min

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water twice
  4. dry with materialThe solvent was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a31ac09fa79418a9a733fb307503a17
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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