Sodium borohydride → 2,2-Difluoro-2-phenylethanol

HRID 271336Notes

Reaction equation

HRID 271336 reaction equation
C([O:3][C:4](=O)[C:5]([F:13])([F:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.[BH4-].[Na+]>C(O)C>[F:12][C:5]([F:13])([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10631860Ethyl 2,2-difluoro-2-phenylacetate

Product 1

HCID 97938912,2-Difluoro-2-phenylethanolYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2.2 g of difluoro-2-phenyl acetic acid ethyl ester (W. J. Middleton, E. M. Bingham, J. Org. Chem., 45, 2883-2887 (1980)), and 0.6 g of sodium borohydride in 75 mL of ethanol was kept at room temperature overnight, concentrated to near dryness under reduced pressure carefully acidified with 20 mL of 5% HCl and extracted into 3×50 mL of dichloromethane. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum gave 1.7 g of product as an oil: 1H NMR (400 MHz, CDCl3) 7.5 (m, 5H), 4.0 (t, 2H).

Workup

  1. concentrationconcentrated
  2. extractionextracted into 3×50 mL of dichloromethane
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customDrying under vacuum

Sources & evidence

ORD record
ord-9e6fbc5b68eb4c49afe95970aca491c6
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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