Water → Methyl 3-fluoro-2-methyl-6-nitrobenzoate

HRID 604262Notes

Reaction equation

HRID 604262 reaction equation
[F:1][C:2]1[C:3]([CH3:14])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:15]([O-])([O-])=O.[Cs+].[Cs+].IC.O>CO>[CH3:15][O:6][C:5](=[O:7])[C:4]1[C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=[C:2]([F:1])[C:3]=1[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 509149483-Fluoro-2-methyl-6-nitrobenzoic acid

Product 1

HCID 59849164Methyl 3-fluoro-2-methyl-6-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-fluoro-2-methyl-6-nitro-benzoic acid in 200 mL of methanol, Cs2CO3 (4.34 g, 13.3 mmol) is added and stirred at the room temperature. The solution is concentrated under reduced pressure then the resulting yellow solids are suspended in 26 ml of DMF. Iodomethane (1.7 ml 26.6 mol) is added at 0° C. and stirred at the room temperature for 30 min. Water is added to the solution and extracted with ethyl acetate. The organic layer is washed with H2O followed by brine, dried over Na2SO4, filtered and evaporated in vacuo to afford 3-fluoro-2-methyl-6-nitro-benzoic acid methyl ester (5.70 g) as yellow oil in quantitative yield. 1H-NMR (400 MHz, δ, ppm) CDCl3: 2.30 (d, 3H), 3.99 (s, 3H), 7.22 (dd, 1H), 8.07 (dd, 1H).

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. stirringstirred at the room temperature for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-7fa4105d5c6a41cf84c05dcb1c7635df
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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