Methyl iodide → 5-Bromo-1,2-dimethyl-3-nitrobenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](O)=O.C(=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[CH3:7][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]=1[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid (287 g, 1100 mmol) in DMF (150 mL), were added sodium carbonate (468 g, 4415 mmol) and methyl iodide (627 g, 4415 mmol). The mixture was heated at 60° C. for 8 h. The precipitate was filtered and washed with diethyl ether (5 times). The combined organic layers were dried, concentrated under reduced pressure giving the title compound (302 g, 99%) which was used directly without further purification.
Workup
- filtrationThe precipitate was filtered
- washwashed with diethyl ether (5 times)
- customThe combined organic layers were dried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1b8b8c030ea543b8b0eb36058fca9760
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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