1,1,3-Trichloropropene → 2-(3,3-Dichloro-2-propenyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile

HRID 749541Notes

Reaction equation

HRID 749541 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][CH:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:6][CH:5]=1.[H-].[Na+].[Cl:20][C:21]([Cl:25])=[CH:22][CH2:23]Cl>CN(C)C=O>[Cl:20][C:21]([Cl:25])=[CH:22][CH2:23][C:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:16])([F:17])[F:1])=[CH:15][CH:14]=1)([C:12]#[N:13])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 173781,1,3-TrichloropropeneHCID 24758Sodium hydrideHCID 22235052(4-(Trifluoromethoxy)benzyl)malononitrile

Product 1

HCID 222349852-(3,3-Dichloro-2-propenyl)-2-(4-(trifluoromethoxy)benzyl)malononitrileYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 0.20 g of (4-(trifluoromethoxy)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 50 mg of sodium hydride (60% in oil), and 0.17 ml of 1,1,3-trichloropropene, and according to the process described in the Production Example 1, there was obtained 80 mg of 2-(3,3-dichloro-2-propenyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (the present compound (28)).

Sources & evidence

ORD record
ord-93b0c78c847d44378843049541461a50
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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