Hydrochloric Acid → HCID 86612546, compound

HRID 1443560Notes

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][C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21].Cl>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[F:1][C:2]([F:18])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:13])[F:12])[CH2:3][C:4]([CH2:21][CH:20]([Br:19])[C:22]([F:25])([F:24])[F:23])([C:7]#[N:8])[C:5]#[N:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1.4 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile was dissolved in 6 ml of a solution (1 mol/L) of tetrabutylammonium fluoride in tetrahydrofuran and then cooled to 0° C. Thereto 1.1 g of 2-bromo-3,3,3-trifluoropropene dissolved in 3 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 8 hours and at 60° C. for 5 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 0.02 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(2-bromo-3,3,3-trifluoropropyl)malononitrile (hereinafter, referred to as the present compound (57)).

Workup

additionwas added dropwise
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-b3dc812194434a08817c045cd7bbecbc
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662402B2

Reaction notes

Loading…