Dimethylformamide → 4,4'-dicyanobenzil

HRID 1176957Notes

Reaction equation

HRID 1176957 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

Reactant 3

HCID 6228DimethylformamideHCID 964304,4'-DibromobenzilHCID 178418260HCID 178418260, compound

Product 1

HCID 109782014,4'-dicyanobenzilYield 48%

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.

Workup

  1. customThe reaction mixture was quenched with a saturated NaCl aqueous solution
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe product was purified by column chromatography (silica gel, dichloromethane:hexanes=5:1 (v/v))
  6. customdried under vacuum at 47° C. overnight

Sources & evidence

ORD record
ord-bcdc7ba046754f889a633a8383a8b179
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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