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

HRID 1870785Notes

Reaction equation

HRID 1870785 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-d029ea2b6ff841ffaa1f03d4c8bd4a5b
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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