Nitrobenzene → HCID 13320616, compound

HRID 259301

Reaction equation

HRID 259301 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1)[CH3:2].Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+]([O-])=O.[N+:20](C1C=CC=CC=1)([O-:22])=[O:21]>C(Cl)Cl.[Cu]>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 7416NitrobenzeneHCID 113411-Bromo-2-nitrobenzeneHCID 1411891-Ethyl-4-iodobenzene

Product 1

HCID 13320616HCID 13320616, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

Copper lining powder (75g) was added portionwise over 30 minutes to a stirred mixture of 1-ethyl-4-iodobenzene (34.8g, 0.15 mole) and 2-bromo-1-nitrobenzene (30.3g, 0.15 mole) in nitrobenzene (250 ml) at 160°. After stirring for a further 3 hours at 160° C the solution was cooled, diluted with methylene chloride and filtered. Methylene chloride was distilled, nitrobenzene was steam-distilled, and the product was isolated in ether, and distilled to give 4-ethyl-2-nitrobiphenyl, b.p. 120°-130° C/0.1mm.

Workup

  1. temperaturewas cooled
  2. filtrationfiltered
  3. distillationMethylene chloride was distilled
  4. distillationnitrobenzene was steam-distilled
  5. customthe product was isolated in ether
  6. distillationdistilled

Sources & evidence

ORD record
ord-e5c9f413df5340fcb9d5060d7b8670e4
Source dataset
uspto-grants-1977_07
Patent number
US04036989

Linked notes

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