Hydrochloric Acid → (4-Chloro-2-fluorophenyl)methanol

HRID 1066532Notes

Reaction equation

HRID 1066532 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.O1CCOCC1.[BH4-].[Na+].Cl>O.CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([F:10])[CH:3]=1

Participants

7

Procedure

First, 25 g of 4-chloro-2-fluorobenzaldehyde was dissolved in a mixed solvent consisting of 250 ml of 1,4-dioxane and 25 ml of methanol, to which 2.4 g of sodium borohydride was added under ice cooling, and the mixture was stirred for 30 minutes. After completion of the reaction, a small amount of diluted aqueous hydrochloric acid was added, and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 25 g of 4-chloro-2-fluorobenzyl alcohol.

Workup

  1. additionwas added under ice cooling
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a3ddbac121614236be6a04c2f7707bbf
Source dataset
uspto-grants-2001_06
Patent number
US06242634B1

Reaction notes

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