Water → Methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate

HRID 2208719Notes

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].[C:18](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C>[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

Conditions

Temperature: 60 °C

Procedure

To stirred solution of 2-methyl-3-nitro-5-(trifluoromethyl)benzoic acid (1 g, 4.01 mmol) in DMF (3 mL) was added sodium carbonate (0.63 g, 6.02 mmol) and methyl iodide (1.14 g, 8.03 mmol). The resulting mixture was heated at 60° C. for 4 h. On completion, water was added to the reaction, and the product extracted using DCM. Combined organic layers were dried, concentrated under reduced pressure and purified by column chromatography over silica to give methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate (1 g, 95.2%).

Workup

extractionthe product extracted
customCombined organic layers were dried
concentrationconcentrated under reduced pressure
custompurified by column chromatography over silica

Sources & evidence

ORD record: ord-de7ddac4ca634bd48838c975638eb2ca
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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