1-Iodo-2-methyl-3-nitrobenzene → 2,2'-Dimethyl-3,3'-dinitrobiphenyl

HRID 846030Notes

Reaction equation

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

Participants

Conditions

Temperature: 230 °C

Procedure

A 20 mL round bottomed flask equipped with a reflux column under argon was charged with 7.05 g of 2-iodo-6-nitrotoluene and 6.55 of copper bronze. The reaction mixture was heated in an oil bath at 230° C. for 9 hours. The mixture was extracted with methylene chloride and the extract filtered. The extract was stripped of solvent and chromatographed on silica gel using carbon tetrachloride as the eluent. In this way 1.71 g (65% yield) of yellowish crystals were obtained.

Workup

customA 20 mL round bottomed flask equipped with a reflux column under argon
extractionThe mixture was extracted with methylene chloride
filtrationthe extract filtered
customchromatographed on silica gel

Sources & evidence

ORD record: ord-4045f0aaafe244b28543e416244195e3
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05135838

Reaction notes

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