tert-Butyl methyl ether → 4-Bromo-1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-Trifluoromethylphenyl Ether
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:15][F:16])([C:13]#[CH:14])[CH2:11][F:12])=[CH:5][CH:4]=1.COC(C)(C)C.CC(C)([O-])C.[K+].[Br:31]Br>CCCCCC.C(O)(C)(C)C>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:11][F:12])([C:13]#[C:14][Br:31])[CH2:15][F:16])=[CH:5][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
An amount (13.9 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl ether was dissolved in a solvent consisting of a mixture of tert-butyl methyl ether (100 ml) and tert-butyl alcohol (150 ml). To the solution under cooling with ice, potassium tert-butoxide (7.1 g) was added under a nitrogen atmosphere; after stirring for a while, bromine (3 ml) was added dropwise. After the end of the dropwise addition, the mixture was stirred for 30 minutes under stirring with ice. Hexane was added to the reaction mixture, which was then washed with water and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (18.1 g).
Workup
- additionwas added under a nitrogen atmosphere
- additionwas added dropwise
- additionAfter the end of the dropwise addition
- stirringunder stirring with ice
- washwas then washed with water
- dry with materialThe mixture was dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-81847dd3e14447bd8eb9f9c76f73b72c
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455708B1
Reaction notes
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