Hydrochloric Acid → 2,2-Difluoro-2-phenylethanol

HRID 1810056Notes

Reaction equation

HRID 1810056 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+].Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10631860Ethyl 2,2-difluoro-2-phenylacetate

Product 1

HCID 97938912,2-Difluoro-2-phenylethanolYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of difluoro-phenyl-acetic acid ethyl ester (5.0 g, 25.0 mmol) in ethanol (150 mL) was added sodium borohydride (1.37 g, 36 mmol) at rt. The mixture was stirred for 2.5 h at room temperature. HCl aqueous (1N) was added and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the product 2,2-difluoro-2-phenyl-ethanol (3.4 g, 86.1%), which was used to the next step without further purification.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cac6f8a26234490e80c741d23e248cd9
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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