Boron trifluoride etherate → Methyl 3-methoxy-4-nitrobenzoate

HRID 1773492Notes

Reaction equation

HRID 1773492 reaction equation
B(F)(F)F.[CH3:5]COCC.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:15]([OH:17])=[O:16]>CO>[CH3:5][O:16][C:15](=[O:17])[C:14]1[CH:18]=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[C:12]([O:11][CH3:10])[CH:13]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoateYield 101.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Boron trifluoride diethyl etherate (2 mL, 16.3 mmol) was added to a suspension of 3-methoxy-4-nitrobenzoic acid (1.0 g, 5.07 mmol) in anhydrous methanol (15 mL) and the resulting mixture was heated at reflux for 24 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between water and dichloromethane; the aqueous layer was extracted 3 times with dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified over a silica gel plug (EtOAc/hexane from 40/60 to 50/50) to give 1.09 g of 3-methoxy-4-nitro-benzoic acid methyl ester as a pale yellow solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between water and dichloromethane
  5. extractionthe aqueous layer was extracted 3 times with dichloromethane
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified over a silica gel plug (EtOAc/hexane from 40/60 to 50/50)

Sources & evidence

ORD record
ord-dff872b5f0cd434c9ecf70fc35849307
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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