Water → HCID 86761604, compound
Reaction equation
[OH:1]S([O-])(=O)=O.[K+].[F:7][C:8]([F:22])([F:21])[C:9]([F:20])([C:16]([F:19])([F:18])[F:17])[CH2:10][CH2:11][S:12][CH2:13][C:14]#[N:15].S([O-])([O-])=O.[Na+].[Na+].[OH2:29]>CO>[F:19][C:16]([F:17])([F:18])[C:9]([F:20])([C:8]([F:7])([F:21])[F:22])[CH2:10][CH2:11][S:12]([CH2:13][C:14]#[N:15])(=[O:1])=[O:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 16.14 g of a double salt of 2 KHSO5.KHSO4.K2SO4 (Oxone, registered trade mark) in 50 ml of water was added dropwise a solution of 4.77 g of (3-(trifluoromethyl)-3,4,4,4-tetrafluorobutylthio)acetonitrile in 50 ml of methanol at room temperature over 60 minutes under a nitrogen atmosphere, and the mixture was stirred for 2 hours. To the reaction mixture was added 50 ml of an aqueous 10% sodium sulfite solution, followed by extraction with 100 ml of ethyl acetate twice. Organic layers were combined, washed with 50 ml of an aqueous 10% sodium sulfite solution and 50 ml of an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under rescued pressure. The residue was subjected to silica gel column chromatography to obtain 4.00 g of (3-(trifluoromethyl)-3,4,4,4-tetrafluorobutylsulfonyl)acetonitrile represented by the formula:
Workup
- extractionfollowed by extraction with 100 ml of ethyl acetate twice
- washwashed with 50 ml of an aqueous 10% sodium sulfite solution and 50 ml of an aqueous saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under rescued pressure
Sources & evidence
- ORD record
- ord-488dcb40acae4efa8d520c0ccb55f616
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247596B2
Reaction notes
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