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

HRID 1684924Notes

Reaction equation

HRID 1684924 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 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20.0 g (0.098 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 portionwise thereto. The mixture is stirred under cold conditions for 1 hour and then the solid is evaporated 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 crystallised from pentane. 18.1 g of compound are obtained.

Workup

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

Sources & evidence

ORD record
ord-ca4daeefeadc4e0284d05a297a0deaf5
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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