Nitrobenzene → 4'-Fluoro-2'-methoxy-4-nitrobiphenyl

HRID 442265Notes

Reaction equation

HRID 442265 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([O:9][CH3:10])[CH:3]=1.[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12].N(OCCC(C)C)=O>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([C:17]2[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 8053Isoamyl NitriteHCID 135322284-Fluoro-2-methoxyaniline

Product 1

HCID 214164654'-Fluoro-2'-methoxy-4-nitrobiphenyl

Procedure

A mixture of 7.7 grams of 4-fluoro-2-methoxyaniline, 200 ml. of nitrobenzene, and 9.0 grams of isoamyl nitrite, is warmed on the steam bath until a vigorous reaction with evolution of gas sets in. This evolution is allowed to proceed without heating until it has subsided, and the mixture is then heated on the steam bath for an additional 3 hours. The excess of nitrobenzene is removed in vacuo. The residue is purified for the desired isomer by elution from a silica gel column using petroleum-benzin to yield 4'-fluoro-2'-methoxy-4-nitrobiphenyl.

Workup

  1. temperaturewithout heating until it
  2. temperaturethe mixture is then heated on the steam bath for an additional 3 hours
  3. customThe excess of nitrobenzene is removed in vacuo
  4. customThe residue is purified for the desired isomer
  5. washby elution from a silica gel column

Sources & evidence

ORD record
ord-538a0af40cf44d548c344234dbeb97e5
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

Loading…