Tetrahydrofuran → (2-Bromo-4,5-difluorophenyl)methanol

HRID 405205Notes

Reaction equation

HRID 405205 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.C1COCC1.[Br:18][C:19]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:20]=1[C:21](O)=[O:22].[BH4-].[Na+]>CCOC(C)=O.C([O-])(O)=O.[Na+].O>[Br:18][C:19]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:20]=1[CH2:21][OH:22]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 27827892-Bromo-4,5-difluorobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 57518297(2-Bromo-4,5-difluorophenyl)methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Solid CDI (4.3 g, 26.4 mmol) was added to a THF solution (130 mL) of 2-bromo-4,5-difluorobenzoic acid and the solution was refluxed. After 3 h the resulting mixture was cooled to room temperature and a water solution (26 mL) of NaBH4 (666 mg, 17.6 mmol) was added. After 10 min the resulting mixture was diluted with EtOAc and 10% aqueous NaHCO3 and the layers were separated. The organic layer was washed with water and brine, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. temperaturethe solution was refluxed
  2. customthe layers were separated
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-bcaba61be42d4a21a7275e925d026b48
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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