Sodium borohydride → 3-Bromo-2-fluorobenzyl Alcohol

HRID 1684918Notes

Reaction equation

HRID 1684918 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 220193613-Bromo-2-fluorobenzaldehyde

Product 1

HCID 269856463-Bromo-2-fluorobenzyl AlcoholYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.00 g of 3-bromo-2-fluorobenzaldehyde are dissolved in 98 ml of methanol; 560 mg of sodium borohydride are added portionwise thereto. The mixture is stirred at ambient temperature for 2 hours and then the solvent is evaporated under reduced pressure. The residue is taken up between water and ethyl acetate and the organic phase is separated, dried and concentrated under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol mixture. 1.56 g of compound are obtained.

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. customthe organic phase is separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-353e33ce6a734bccb2cc1491d02fb782
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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