Methanol → Methyl 3-nitro-5-(trifluoromethyl)benzoate

HRID 1050116Notes

Reaction equation

HRID 1050116 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:22]O>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:7]([O:9][CH3:22])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoateYield 90%

Conditions

Temperature
25 °C

Procedure

To a mixture of 3-nitro-5-(trifluoromethyl)benzoic acid (20 g, 85 mmol) in MeOH (200 mL) was added H2SO4 (12 mL, 225 mmol) at 0° C. dropwise, then the mixture was stirred for 16 h at 25° C. Then the solvent was concentrated and was adjusted pH=9 with NaHCO3 solution. The solvent was concentrated to give the residue which was extracted with DCM (200 mL×2), dried over Na2SO4, filtered, and concentrated to yield an oil of methyl 3-nitro-5-(trifluoromethyl)benzoate (20 g, 76 mmol, 90% yield): 1H NMR (400 MHz, CD3OD) δ 8.99 (s, 1H), 8.74 (s, 1H), 8.62 (s, 1H), 4.01 (s, 3H); ES-LCMS m/z 250 (M+1).

Workup

  1. concentrationThen the solvent was concentrated
  2. concentrationThe solvent was concentrated
  3. customto give the residue which
  4. extractionwas extracted with DCM (200 mL×2)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-926fbc138e8d496c952bdef157dd9ea7
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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