Hydrochloric Acid → 2,2-Difluoro-2-phenylethanol
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe resulting mixture was extracted with dichloromethane
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cac6f8a26234490e80c741d23e248cd9
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362049B2
Reaction notes
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