Hydrochloric Acid → 2-(3-Bromopropyl)-2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile
Reaction equation
[F:1][C:2]([F:18])([C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])[CH2:3][CH:4]([C:7]#[N:8])[C:5]#[N:6].[Br:19][CH2:20][CH2:21][CH2:22]Br.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Br:19][CH2:20][CH2:21][CH2:22][C:4]([CH2:3][C:2]([F:18])([F:1])[C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:13])[F:12])([C:7]#[N:8])[C:5]#[N:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3.2 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile and 8.6 g of 1,3-dibromopropane were dissolved in 20 ml of dimethyl sulfoxide, 3.0 g of potassium carbonate was added, and the mixture was stirred at room temperature for 2 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with methyl tert-butyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.2 g of 2-(3-bromopropyl)-2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile (hereinafter, referred to as the present compound (65)).
Workup
- extractionfollowed by extraction with methyl tert-butyl ether
- washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4e035ce0af4b4b2bba975d93fb4a1d23
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662402B2
Reaction notes
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