Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate → Ethyl 4,4,4-trifluoro-3-methyl-2-[4-(2,2,2-trifluoroethyl)phenyl]butanoate
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1>CN1CCCC1=O.[Cu]I>[F:17][C:16]([F:19])([F:18])[CH:15]([CH3:20])[CH:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:5]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
529 mg (2.78 mmol) of copper(I) iodide and 4 g (20.82 mmol) of methyl 2,2-difluoro-2-(fluorosulphonyl) acetate were added to 3.77 g (10.67 mmol) of ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate in 40 ml of 1-methylpyrrolidin-2-one, and the mixture was stirred at 80° C. overnight. After the reaction had gone to completion, the reaction solution was slowly poured onto 100 ml of ice-water. The mixture obtained was then extracted three times with diethyl ether. The combined organic phases were dried over magnesium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/dichloromethane 4:1). This gave 1.48 g (4.32 mmol, 41% of theory) of the title compound as a yellowish oil.
Workup
- customThe mixture obtained
- extractionwas then extracted three times with diethyl ether
- dry with materialThe combined organic phases were dried over magnesium sulphate
- filtrationAfter filtration
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-b994c667ebf7434ca717c2e3cc4ea729
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018414B2
Reaction notes
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