Toluene → Ethyl 2-ethoxy-4-fluorobenzoate

HRID 2068972Notes

Reaction equation

HRID 2068972 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[C:12]1(C)C=CC=C[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:29][CH3:30])(=O)=O>COC(C)(C)C>[CH2:12]([O:11][C:4]1[CH:3]=[C:2]([F:1])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:29][CH3:30])=[O:7])[CH3:13]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 676614-Fluorosalicylic acid

Product 1

HCID 59198761Ethyl 2-ethoxy-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a liquid mixture of 4-fluoro-2-hydroxybenzoic acid 5.00 g, toluene 32 mL and potassium carbonate 13.29 g, diethyl sulfate 12.6 mL was dropped, followed by an hour's stirring at room temperature and further addition of 25 mL of toluene. After 16 hours' heating under reflux, the reaction liquid was allowed to cool off, to which tert-butyl methyl ether was added and the whole liquid was poured in ice water. The organic layer was extracted, washed with saturated brine and dried over magnesium sulfate. Distilling the solvent off, 6.52 g of the title compound was obtained.

Workup

  1. additionwas dropped
  2. waitfollowed by an hour
  3. temperatureAfter 16 hours' heating
  4. temperatureunder reflux
  5. customthe reaction liquid
  6. additionwas added
  7. extractionThe organic layer was extracted
  8. washwashed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. distillationDistilling the solvent off, 6.52 g of the title compound
  11. customwas obtained

Sources & evidence

ORD record
ord-713df22ac96a4f8e9785a7088dc0c9de
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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