Azobisisobutyronitrile → HCID 86683909, compound

HRID 2405011Notes

Reaction equation

HRID 2405011 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+]([O-])=O)=[CH:4][C:3]=1[CH3:11].[Br:12][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:12][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].[C:3]1([CH3:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 86683909HCID 86683909, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

905 g (5.83 mol) of 2-fluoro-5-nitrotoluene and 1038 g (5.83 mol) of N-bromosuccinimide were introduced as initial charge in 5.83 l of chloroform, 47.8 g (0.29 mol) of 2,2′-azobis[isobutyronitrile] were added and the reaction mixture was heated at reflux for 18 h. After cooling to RT, the liquid was filtered off from the solid by suction and the filtrate was divided into three portions. These were absorbed in each case on 1.5 kg of silica gel (0.06-0.2) and chromatographically purified on in each case 10 kg of silica gel with 160 l of ethyl acetate:petroleum ether (2.5:97.5). The product fractions were combined and evaporated to dryness on a rotary evaporator, and the residue was extracted by stirring with petroleum ether for 10 min. The solid was filtered off with suction, after-washed with petroleum ether and dried in vacuo. 385 g (28%) were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. filtrationthe liquid was filtered off from the solid by suction
  4. customThese were absorbed in each case on 1.5 kg of silica gel (0.06-0.2)
  5. customchromatographically purified on in each case 10 kg of silica gel with 160 l of ethyl acetate:petroleum ether (2.5:97.5)
  6. customevaporated to dryness on a rotary evaporator
  7. extractionthe residue was extracted
  8. filtrationThe solid was filtered off with suction
  9. washafter-washed with petroleum ether
  10. customdried in vacuo
  11. custom385 g (28%) were obtained

Sources & evidence

ORD record
ord-4a1074b759de429c8a92f2384f515da3
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

Loading…