4-(Trifluoromethoxy)benzalmalononitrile → HCID 22235037, compound

HRID 1743624Notes

Reaction equation

HRID 1743624 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:6][CH:5]=1.[CH3:18][Mg]Br>O1CCCC1.[Cu]I>[F:1][C:2]([F:16])([F:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]([CH:9]([C:12]#[N:13])[C:10]#[N:11])[CH3:18])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 8456624-(Trifluoromethoxy)benzalmalononitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 22235037HCID 22235037, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Using 1.19 g of (4-(trifluoromethoxy)benzylidene)malononitrile, 20 ml of tetrahydrofuran, a catalytic amount of copper (1) iodide, and 12.5 ml of a solution of methyl magnesium bromide in tetrahydrofuran (about 1 M, available from Tokyo Kasei Kogyo Co., Ltd), and according to the process described in REFERENCE PRODUCTION EXAMPLE 2, there was obtained 0.76 g of (1-(4-(trifluoromethoxy)phenyl)ethyl)malononitrile (the intermediate (10)).

Sources & evidence

ORD record
ord-fd8a9aa424554254a9d4f26d7e2b71a5
Source dataset
uspto-grants-2006_03
Patent number
US07011838B2

Reaction notes

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