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

HRID 1881118Notes

Reaction equation

HRID 1881118 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-364658702f8f4c9090de7765b4c86ee5
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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