Methyl iodide → Methyl 5-fluoro-3-methyl-2-nitrobenzoate

HRID 2369885Notes

Reaction equation

HRID 2369885 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:15](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 534307765-Fluoro-3-methyl-2-nitrobenzoic acid

Product 1

HCID 53415166Methyl 5-fluoro-3-methyl-2-nitrobenzoateYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-fluoro-3-methyl-2-nitrobenzoic acid (8.0 g, 40 mmol) from Step A above in DMF (100 mL) was added cesium carbonate (20.0 g, 60 mmol) followed by iodomethane (3.0 ml, 48 mmol). The reaction solution was stirred at ambient temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo to afford methyl 5-fluoro-3-methyl-2-nitrobenzoate (8.4 g, 98%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.71-7.67 (m, 2H), 3.85 (s, 3H), 2.32 (s, 3H); MS (ESI+) m/z 214 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. customwas separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2731dd0f5218416f99b71e157f65f288
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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