Dimethylformamide → 4,4'-dicyanobenzil

HRID 1176949Notes

Reaction equation

HRID 1176949 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[Cu](C#N)[C:20]#[N:21].[CH3:24][N:25](C=O)C>>[C:20]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:24]#[N:25])=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1)#[N:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 964304,4'-Dibromobenzil2×HCID 178418260HCID 178418260, compound

Product 1

HCID 109782014,4'-dicyanobenzilYield 48%

Procedure

Here we have discovered that the compound can be easily synthesized from commercially available 4,4′-dibromobenzil. The reaction between 4,4′-dibromobenzil and copper cyanide in DMF at 165° C. yielded 4,4′-dicyanobenzil (JYC-I-097-A) as a yellow solid (1.36 g, 48%) after column chromatography. The scheme of the reaction is shown in FIG. 12.

Sources & evidence

ORD record
ord-039f4329f7f94b19991756b79995d8cb
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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