Sodium borohydride → Tert-butyl 3,5-difluoro-4-(hydroxymethyl)benzoate

HRID 83888Notes

Reaction equation

HRID 83888 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:17])[C:14]=1[CH:15]=[O:16])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:17])[C:14]=1[CH2:15][OH:16])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21924996Tert-butyl 3,5-difluoro-4-formylbenzoate

Product 1

HCID 66740404Tert-butyl 3,5-difluoro-4-(hydroxymethyl)benzoateYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 3,5-difluoro-4-formylbenzoate (21 g, 86.7 mmol) in MeOH was portionwise added NaBH4 (3.28 g, 86.7 mmol) at 0° C. After 20 min, the reaction mixture was evaporated in vacuo and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography (Hex/EtOAc=4:1) to give tert-butyl 3,5-difluoro-4-(hydroxymethyl)benzoate (20.7 g, 97%) as a white solid.

Workup

  1. customat 0° C
  2. customthe reaction mixture was evaporated in vacuo
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (Hex/EtOAc=4:1)

Sources & evidence

ORD record
ord-9966468f3ca74f5d96354be255cc0e74
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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