Sodium borohydride → (3-Bromo-2,6-difluorophenyl)methanol

HRID 2196458Notes

Reaction equation

HRID 2196458 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH2:5][OH:6])[C:7]([F:10])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 221397013-Bromo-2,6-difluorobenzaldehyde

Product 1

HCID 22219889(3-Bromo-2,6-difluorophenyl)methanolYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g of 3-bromo-2,6-difluorobenzaldehyde are dissolved in 450 ml of methanol and cooled in an ice bath; 3.42 g of sodium borohydride are then added thereto, portionwise. The mixture is stirred at ambient temperature for 1 hour and the solvent is then evaporated off under reduced pressure. The residue is taken up between water and dichloromethane. The organic phase is separated, dried and concentrated under reduced pressure. The residue is crystallized from n-pentane. 14.6 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 n-pentane

Sources & evidence

ORD record
ord-d825961f40a24530a3580e1626df1677
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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