4-Bromo-2-fluorobenzaldehyde → (4-Bromo-2-fluorophenyl)methanol

HRID 1992376Notes

Reaction equation

HRID 1992376 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[BH4-].[Na+]>CO.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2734027(4-Bromo-2-fluorophenyl)methanolYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-bromo-2-fluorobenzaldehyde (25 g, 0.123 mol) in methanol (250 ml) was added NaBH4 (7.02 g, 0.1847 mol) and the reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with 25 ml of water and solvent evaporated under reduced pressure. The compound was extracted with ethyl acetate, organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure afforded the sub-title compound (25 g) as an oil. This was directly taken for next step without further purification.

Workup

  1. customevaporated under reduced pressure
  2. extractionThe compound was extracted with ethyl acetate, organic layer
  3. washwas washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-677328e161de43ca9f1565afdd5ad95a
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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