Iodobenzene → Methyl 3,5-dinitro-4-phenylbenzoate

HRID 1605540Notes

Reaction equation

HRID 1605540 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Cu]>[N+:15]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:6]([O:8][CH3:9])=[O:7])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 11575IodobenzeneHCID 96161Methyl 4-chloro-3,5-dinitrobenzoate

Product 1

HCID 21546857Methyl 3,5-dinitro-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of methyl 4-chloro-3,5-dinitrobenzoate (60 g), iodobenzene (36 ml) and copper powder (60 g) is stirred at 145°-155° C for 4-5 hours. After cooling, the resulting solids are extracted with three portions of boiling chloroform (each portion 150 ml), and the combined extracts are, after filtration, evaporated in vacuo. After trituration of the residue with methanol (150 ml) followed by recrystallization from 2-methoxyethanol, methyl 3,5-dinitro-4-phenylbenzoate is obtained with a melting point of 147.5°-148° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting solids are extracted with three portions of boiling chloroform (each portion 150 ml), and the combined extracts
  3. filtrationafter filtration
  4. customevaporated in vacuo
  5. customAfter trituration of the residue with methanol (150 ml) followed by recrystallization from 2-methoxyethanol

Sources & evidence

ORD record
ord-dc5bb42f2fb24000b6eba0bb2dbf472e
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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