5-Bromo-2-fluorobenzaldehyde → (5-Bromo-2-fluorophenyl)methanol

HRID 2042914Notes

Reaction equation

HRID 2042914 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

4

Reactant 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2773352(5-Bromo-2-fluorophenyl)methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (30.0 g, 148 mmol) in EtOH was added sodium borohydride (8.39 g, 222 mmol) at 0° C. The resulting mixture was stirred with gradual warming to ambient temperature over 15 h, re-cooled to 0° C., and quenched with aq. saturated NH4Cl solution. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo to yield the titled compound (30.3 g, quantitative) as a white sold, which was carried on to the next step without further purification.

Workup

  1. temperaturere-cooled to 0° C.
  2. customquenched with aq. saturated NH4Cl solution
  3. extractionThe mixture was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-175faa5500d74e8499bd760bfd4f48e9
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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