Dimethylformamide → 4,4'-Dicyanobenzil
Reaction equation
[Cu]([C:4]#[N:5])C#N.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)=[O:16])=[O:14])=[CH:9][CH:8]=1.[CH3:24][N:25](C=O)C>>[C:24]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:4]#[N:5])=[CH:19][CH:18]=2)=[O:16])=[O:14])=[CH:9][CH:8]=1)#[N:25]Participants
4
Conditions
- Temperature
- 165 °C
Procedure
A mixture of copper cyanide (2.53 g, 28.3 mmol) and 4,4′-dibromobenzil (4.0 g, 10.9 mmol) in 60 mL of DMF was refluxed at 165° C. for 1 day. The reaction mixture was quenched with a saturated NaCl aqueous solution and extracted with diethyl ether. The combined organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The product was purified by column chromatography (silica gel, dichloromethane:hexanes=5:1 (v/v)) and dried under vacuum at 47° C. overnight to give a yellow solid (1.36 g, 48%). 1H NMR (300 MHz, CDCl3, δ): 8.09 (d, J=8.3 Hz, 4H), 7.83 (d, J=8.8 Hz, 4H). 13C{1H} NMR (75 MHz, CDCl3, δ): 190.76, 135.27, 132.85, 130.36, 118.36, 117.40. HRMS-EI (m/z): [M]+ calcd for C16H8N2O2, 260.0586; found, 260.0580. Anal. Calcd for C16H8N2O2: C, 73.84; H, 3.10; N, 10.76. Found: C, 73.79; H, 2.99; N, 10.75.