Sodium hydride → 2-(4-Cyanobenzyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrile

HRID 749576Notes

Reaction equation

HRID 749576 reaction equation
[F:1][C:2](=[C:10]([F:12])[F:11])[CH2:3][CH2:4][CH:5]([C:8]#[N:9])[C:6]#[N:7].[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=1>CN(C)C=O>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C:5]([CH2:4][CH2:3][C:2]([F:1])=[C:10]([F:11])[F:12])([C:6]#[N:7])[C:8]#[N:9])=[CH:18][CH:19]=1)#[N:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 22185753(3,4,4-Trifluoro-3-butenyl)malononitrile

Product 1

HCID 222350162-(4-Cyanobenzyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrileYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 0.20 g of (3,4,4-trifluoro-3-butenyl)malononitrile, 5 ml of N,N-dimethylformamide, 50 mg of sodium hydride (60% in oil), and 0.25 g of α-bromo-p-tolunitrile, and according to the process described in the Production Example 1, there was obtained 0.21 g of 2-(4-cyanobenzyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrile (the present compound (68)).

Sources & evidence

ORD record
ord-a9f26522052c41c0ab13be38eb96bd6c
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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