Methyl iodide → Methyl 3-methoxy-5-nitrobenzoate

HRID 1515561Notes

Reaction equation

HRID 1515561 reaction equation
CI.[OH:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[C:17](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:17][O:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 239344Methyl 3-hydroxy-5-nitrobenzoate

Product 1

HCID 877382Methyl 3-methoxy-5-nitrobenzoateYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl iodide (0.200 mL, 3.2 mmol), 93A (328 mg, 1.66 mmol), and potassium carbonate (250 mg, 1.80 mmol) in DMF (2 mL) was stirred overnight at rt. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were washed with water and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient of 0 to 50% ethyl acetate in hexanes) to give 93B (0.22 g, 63%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.95 (s, 3H) 3.98 (s, 3H) 7.87-7.90 (m, 1H) 7.90-7.93 (m, 1H) 8.44-8.48 (m, 1H); LC/MS 212 (M+H).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with water
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (gradient of 0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a35056a494bb4974862623f1b36e7e3a
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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