Sodium borohydride → [2-Fluoro-3-(trifluoromethoxy)phenyl]methanol

HRID 623506Notes

Reaction equation

HRID 623506 reaction equation
[F:1][C:2]1[C:9]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[F:1][C:2]1[C:9]([O:10][C:11]([F:13])([F:14])[F:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 459337302-Fluoro-3-(trifluoromethoxy)benzaldehyde

Product 1

HCID 15582606[2-Fluoro-3-(trifluoromethoxy)phenyl]methanolYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-fluoro-3-(trifluoromethoxy)benzaldehyde (1.00 g, 4.81 mmol) in methanol (20 mL) is added Sodium borohydride (0.36 g, 9.61 mmol) at 0° C. After stirring at room temperature for 16 hours, the reaction mixture is quenched with water. The mixture is diluted with ethyl acetate (100 mL) and washed with water. The organic layer is dried over sodium sulfate, and concentrated under reduced pressure to give 0.97 g (96% yield) of the title compound as colorless syrup. This material is used for the next reaction (Step-2) without further purification.

Workup

  1. customthe reaction mixture is quenched with water
  2. additionThe mixture is diluted with ethyl acetate (100 mL)
  3. washwashed with water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a82fb37a746443e8192358170810466
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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