Dimethyl Sulfoxide → HCID 86612542, compound

HRID 1443555Notes

Reaction equation

HRID 1443555 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][CH:5]([C:8]#[N:9])[C:6]#[N:7].[Br:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Br:12][CH2:13][C:5]([CH2:4][CH2:3][C:2]([F:10])([F:11])[F:1])([C:8]#[N:9])[C:6]#[N:7]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrile

Product 1

HCID 86612542HCID 86612542, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.2 g of 2-(3,3,3-trifluoropropyl)malononitrile, 7.0 g of dibromomethane and 5.5 g of potassium carbonate were added to 40 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 18 hours. Thereafter, the reaction mixture was poured to water and then extracted with diethyl ether. The organic layer was washed successively with water and aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.4 g of 2-bromomethyl-2-(3,3,3-trifluoropropyl)malononitrile (hereinafter, referred to as the present compound (52)).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed successively with water and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15d11082f1e4438cb30a0971afc1ef3f
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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