Methyl iodide → Methyl 5-chloro-2-methyl-3-nitrobenzoate
Reaction equation
[Cl: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]([OH:9])=[O:8].[C:15](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[Cl: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:9][CH3:15])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 5-chloro-2-methyl-3-nitrobenzoic acid (23.5 g, 0.109 mmol) in DMF (120 mL) was added sodium carbonate (46.21, 0.436 mmol) and methyl iodide (27.2 mL, 0.43 mmol) at room temperature. The reaction mixture was heated at 60° C. for 3 h. After complete consumption of starting material the reaction mixture was filtered and the residue washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the crude product purified by column chromatography to provide the desired compound (16 g, 64%) as thick oil which solidified on standing.
Workup
- customAfter complete consumption of starting material the reaction mixture
- filtrationwas filtered
- washthe residue washed with ethyl acetate
- concentrationThe filtrate was concentrated under reduced pressure
- customthe crude product purified by column chromatography
Sources & evidence
- ORD record
- ord-409ab5041e9340d5a69933da13644ee0
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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