1-Bromo-2-nitrobenzene → HCID 12529833, compound

HRID 972889Notes

Reaction equation

HRID 972889 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]>[N+](C1C=CC=CC=1)([O-])=O.[Cu]>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1

Participants

5

Reactant 2

HCID 113411-Bromo-2-nitrobenzeneHCID 770041,4-Dibromo-2-nitrobenzene

Product 1

HCID 12529833HCID 12529833, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

2-Bromonitrobenzene (Beilstein, Vol. 5, p.247; 58g) and 2,5-dibromonitrobenzene (Beilstein, vol. 5 p.250; 81g) in nitrobenzene (250 ml.) were heated at 170°-180° C. while copper powder (70 g.) was added over 15 minutes. The reaction mixture was stirred at 180° C. for 15 minutes, cooled and filtered, and the filtrate evaporated under reduced pressure. The residue was extracted into chloroform, the extract dried and evaporated, and the solid recrystallised several times from methanol to give 4-bromo-2,2'-dinitrobiphenyl, m.p. 145°-147° C. (Found: Br, 24.6 C12H7BrN2O4 requires Br, 24.8%).

Workup

  1. additionwas added over 15 minutes
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure
  5. extractionThe residue was extracted into chloroform
  6. customthe extract dried
  7. customevaporated
  8. customthe solid recrystallised several times from methanol

Sources & evidence

ORD record
ord-26e82d33d3144cacb189772e17c9ddaa
Source dataset
uspto-grants-1977_10
Patent number
US04053639

Reaction notes

Loading…