Iodobenzene → 2-Nitro-biphenyl-4-carboxylic acid methyl ester

HRID 2197969

Reaction equation

HRID 2197969 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Br)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl.[Cu]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[O:14]

Participants

5

Reactant 2

HCID 11575IodobenzeneHCID 2736829Methyl 4-bromo-3-nitrobenzoate

Product 1

HCID 121698042-Nitro-biphenyl-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
218 °C

Procedure

The product from Example 212a (0.100 g, 0.384 mmol) was combined with iodobenzene (0.375 mL, 3.35 mmol) and copper powder (0.188 g, 2.96 mmol) and the mixture heated in a sealed tube to 218° C. for 90 minutes. The reaction mixture was subsequently diluted with dichloromethane and filtered through celite. The crude product, obtained by concentration under vacuum, was purified by flash chromatography on silica gel (ethyl acetate-hexanes) to give the title compound (0.0847 g, 86

Workup

  1. filtrationfiltered through celite
  2. customThe crude product, obtained by concentration under vacuum
  3. customwas purified by flash chromatography on silica gel (ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-01183dc54b6843229ea331f613fd02dc
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Linked notes

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