Sodium borohydride → (2-Bromo-6-fluorophenyl)methanol

HRID 2196457Notes

Reaction equation

HRID 2196457 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 224739772-Bromo-6-fluorobenzaldehyde

Product 1

HCID 44181801(2-Bromo-6-fluorophenyl)methanolYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20.0 g (0098 mol) of 2-bromo-6-fluorobenzaldehyde are dissolved in 500 ml of methanol and cooled in an ice bath; 3.72 g (0.098 mol) of sodium borohydride are then added thereto, portionwise. The mixture is stirred under cold conditions for 1 hour and the solvent is then evaporated off under reduced pressure. The residue is taken up between water and dichloromethane, and the organic phase is separated, dried and concentrated under reduced pressure. The residue is crystallized from pentane. 18.1 g of compound are obtained.

Workup

  1. temperaturecooled in an ice bath
  2. customthe solvent is then evaporated off under reduced pressure
  3. customthe organic phase is separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is crystallized from pentane

Sources & evidence

ORD record
ord-3b776c9206ec4bdf9851abee129f4ea4
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

Loading…