Methyl 2-chloro-5-nitrobenzoate → Dimethyl 4,4'-dinitro[1,1'-biphenyl]-2,2'-dicarboxylate
Reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>[Cu]>[C:4]([C:3]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:2]=1[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])([O:6][CH3:7])=[O:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 220 °C
Procedure
A mixture of methyl 2-chloro-5-nitrobenzoate (66.5 g, 0.309 mol) and sand (200 g) is added to a 500 ml, three-necked round-bottom flask equipped with an overhead stirrer, condenser and a nitrogen inlet tube. After the mixture is heated to 220° C. under nitrogen with stirring, activated copper (50.0 g) is added gradually during 1 hour. The reaction mixture is stirred at 220° C. under nitrogen for another 3 hours, and the mixture is then extracted with boiling acetone, and filtered while hot to remove copper and sand. The acetone is thereafter removed from the filtrate under reduced pressure. The residue is recrystallized from methanol two times to yield 45 percent of yellow crystals: mp 176.5°-177.0° C.
Workup
- additionis added to a 500 ml, three-necked round-bottom flask
- customequipped with an overhead stirrer, condenser and a nitrogen inlet tube
- stirringThe reaction mixture is stirred at 220° C. under nitrogen for another 3 hours
- extractionthe mixture is then extracted with boiling acetone
- filtrationfiltered while hot
- customto remove copper and sand
- customThe acetone is thereafter removed from the filtrate under reduced pressure
- customThe residue is recrystallized from methanol two times
Sources & evidence
- ORD record
- ord-4aad5c7bf2b443c58cf51eb2b8b49134
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05491200
Reaction notes
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