Dimethylformamide → Methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate
Reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:18]N(C=O)C.IC.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:15])([F:16])[F:17])=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of 2-methyl-3-nitro-5-(trifluoromethyl)benzoic acid (1 equiv.) in DMF (3 ml per 1 mmol), iodomethane (4 equiv.) and sodium carbonate (4 equiv.) were added. The resulting reaction mixture was stirred at 60° C. for 8 h. On completion, reaction mixture was filtered and the inorganic solid residue washed with ethyl acetate. The combined filtrate was concentrated under vacuum till dryness and the residue re-dissolved in ethyl acetate before washing with 5% sodium bicarbonate solution followed by 5M HCl solution, the organic layer was finally washed with brine, dried over sodium sulfate and concentrated to afford pure methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate (yield 90-95%).
Workup
- customThe resulting reaction mixture
- customOn completion, reaction mixture
- filtrationwas filtered
- washthe inorganic solid residue washed with ethyl acetate
- concentrationThe combined filtrate was concentrated under vacuum till dryness
- dissolutionthe residue re-dissolved in ethyl acetate
- washbefore washing with 5% sodium bicarbonate solution
- washthe organic layer was finally washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0e4b05bda15f418fa279799b30444eb5
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206157B2
Reaction notes
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