Water → [3-Fluoro-4-(methylsulfanyl)phenyl]methanol

HRID 1597576Notes

Reaction equation

HRID 1597576 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10][CH3:11])[CH:5]=[O:6].[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[S:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 112752573-Fluoro-4-(methylthio)benzaldehyde

Product 1

HCID 22316885[3-Fluoro-4-(methylsulfanyl)phenyl]methanolYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 3-fluoro-4-(methylsulfanyl)benzaldehyde (19.44 g, 114.2 mmol) and sodium borohydride (2.1 g, 55.46 mmol) in methanol (200 mL) was stirred at room temperature for 2 hour. Water was added to the mixture, and the mixture was evaporated, diluted with ethyl acetate (300 mL), washed with water (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/4) to provide the subtitle compound (19.91 g, 100% yield) as an oil.

Workup

  1. customthe mixture was evaporated
  2. additiondiluted with ethyl acetate (300 mL)
  3. washwashed with water (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/4)

Sources & evidence

ORD record
ord-211803eadc404baa9153fff207a069e2
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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