Dimethylformamide → 4-Formyl-2-nitrobenzonitrile

HRID 401200

Reaction equation

HRID 401200 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].CCOC(C)=O.[CH3:19][N:20](C)C=O>>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:19]#[N:20])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)=[O:7]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 8087924-Bromo-3-nitrobenzaldehyde

Product 1

HCID 221178154-Formyl-2-nitrobenzonitrileYield 56.1%

Procedure

A mixture of 4-bromo-3-nitrobenzaldehyde (1 g, 4.35 mmol) in dimethylformamide (10 mL) was added cuprous cyanide (584.8 mg, 6.53 mmol). The resultant solution was stirred at 160° C. for 5 hours. After cooling, a standard aqueous/EtOAc workup was followed. Purified by silica gel column chromatography to give product (430 mg, yield 56.1%).

Workup

  1. temperatureAfter cooling
  2. customPurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e07eb1dbf2fb4ad7a2790904e0842bc3
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Linked notes

Loading…