2-Iodo-3-nitrotoluene → 2,2'-Dinitro-6,6'-dimethylbiphenyl

HRID 1493545Notes

Reaction equation

HRID 1493545 reaction equation
I[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11]>[Cu]>[CH3:11][C:3]1[C:2]([C:2]2[C:3]([CH3:11])=[CH:4][CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 2347812-Iodo-3-nitrotoluene

Product 1

HCID 2929672,2'-Dinitro-6,6'-dimethylbiphenylYield 73%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

In an eggplant flask having a ground-in stopper and equipped with a condenser were charged 2-iodo-3-nitrotoluene (6) as obtained in Preparation Example 3 and an equivalent weight of a copper powder, and the contents were stirred in an oil bath at 200° C. for 10 hours. The mixture was extracted with benzene by means of a Soxhlet extractor. The solvent was removed from the extract by distillation under reduced pressure, and the resulting crude crystal was recrystallized from 99% ethanol to obtain 6,6'-dimethyl-2,2'-dinitro-1,1'-biphenyl (7) as a black needle-like crystal having a melting point of 107.4° to 108.3° C. and a 73% yield.

Workup

  1. customIn an eggplant flask having
  2. customa ground-in stopper and equipped with a condenser
  3. customas obtained in Preparation Example 3
  4. extractionThe mixture was extracted with benzene by means of a Soxhlet extractor
  5. customThe solvent was removed from the
  6. extractionextract by distillation under reduced pressure
  7. customthe resulting crude crystal was recrystallized from 99% ethanol

Sources & evidence

ORD record
ord-c381e7f04ddd46c3882b62cedf1bac6a
Source dataset
uspto-grants-1991_06
Patent number
US05021593

Reaction notes

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