Hydrochloric Acid → HCID 22666446, compound

HRID 1007948Notes

Reaction equation

HRID 1007948 reaction equation
Br[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[C:10]([O:18][C:19]([CH3:22])(C)C)(=[O:17])[CH2:11][C:12](OCC)=O.Cl.[F:24][C:25]1[C:33]([F:34])=C(F)[C:31]([F:36])=[CH:30][C:26]=1[C:27]([OH:29])=[O:28]>CS(C)=O.C1(C)C=CC=CC=1.O>[CH2:2]([O:29][C:27]([C:26]1[CH:30]=[C:31]([F:36])[C:12]([CH2:11][C:10]([O:18][CH2:19][CH3:22])=[O:17])=[C:33]([F:34])[C:25]=1[F:24])=[O:28])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 11430Potassium Carbonate2×HCID 96345tert-Butyl ethyl malonateHCID 2975492,3,4,5-Tetrafluorobenzoic acid

Product 1

HCID 22666446HCID 22666446, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

In 50 mL of dimethyl sulfoxide is dissolved 2,3,4,5-tetrafluorobenzoic acid, to which are added 4.6 mL of bromoethane and 8.19 g of potassium carbonate. The mixture is stirred at 70° C. for 2 hours. Then, 18.52 g of potassium carbonate and 15.02 g of tert-butyl ethyl malonate, and the mixture is stirred at 90° C. for 2 hours. Water and toluene are added to the reaction mixture, pH is adjusted to 4 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water, saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is dissolved in 50 mL of toluene and heated under reflux for 3.5 hours together with 0.2 g of p-toluenesulfonic acid monohydrate. Water and ethyl acetate are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. By distilling off the solvent under reduced pressure, there is obtained 15.2 g of ethyl 4-ethoxycarbonyl-2,3,6-trifluorophenylacetate.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water, saturated aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. dissolutionthe residue is dissolved in 50 mL of toluene
  6. temperatureheated
  7. temperatureunder reflux for 3.5 hours together with 0.2 g of p-toluenesulfonic acid monohydrate
  8. additionWater and ethyl acetate are added to the reaction mixture
  9. customthe organic layer is separated
  10. washThe organic layer is washed with water, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationBy distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-9123813231e24943b7234e0acf2c047b
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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