Sodium Bicarbonate → Methyl 4-nitro-3-(trifluoromethyl)benzoate

HRID 1161353Notes

Reaction equation

HRID 1161353 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([O-:3])=[O:2].[C:17](=O)(O)[O-].[Na+]>Cl.CO>[CH3:17][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 162177534-Nitro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 46311177Methyl 4-nitro-3-(trifluoromethyl)benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The solution of 4.2 g (17.9 mmol) 4-nitro-3-(trifluoromethyl)benzoic acid (commercially available) in 5.1 mL 1.25 M hydrochloric acid in methanol was refluxed for 5 h. After cooling down to room temperature the solution was poured on saturated aqueous sodium bicarbonate solution and the phases were separated. The aqueous layer was extracted three times with ethyl acetate, the combined organic layers washed with brine, dried over magnesium sulfate and evaporated. After filtration the solvent was evaporated and the residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (100:0 to 60:40 v/v) to afford the title compound as a light yellow solid (90%) which was pure enough for the next step without further purification.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. filtrationAfter filtration the solvent
  7. customwas evaporated
  8. customthe residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.)
  9. washeluting with a gradient of heptane:ethyl acetate (100:0 to 60:40 v/v)

Sources & evidence

ORD record
ord-7e8d1210e6b04f4f8d6937a5266e6689
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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