Réaction #2358486

ord-111c605a61134ec3ae46115e80cc1207

Équation de réaction

O=Cc1ccc(C(F)(F)F)cc1F
2-fluoro-4-(trifluoromethyl)benzaldehyde
COC(=O)CS
methyl thioglycolate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
DMF
COC(=O)c1cc2ccc(C(F)(F)F)cc2s1
methyl-6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate
Rendement 56.4%

Solvants

Conditions de réaction

Température
140°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurethe reaction mixture was cooled to room temperature
  2. 2
    Extractionextracted with tert-butyl methyl ether 3 times
  3. 3
    LavageThe combined organic layer was washed with water
  4. 4
    SéchageThe mixture was dried over magnesium sulfate
  5. 5
    Concentrationconcentrated under reduced pressure

Mode opératoire

A mixture of 1.11 g of 2-fluoro-4-(trifluoromethyl)benzaldehyde, 739 mg of methyl thioglycolate, 1.3 g of potassium carbonate and 20 ml of DMF was stirred at 140° C. for 2 hours, and then the reaction mixture was cooled to room temperature. To the reaction mixture was added water, and then extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with water, followed by saturated aqueous sodium chloride solution. The mixture was dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 848 mg of methyl-6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (the present compound 2).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09119396B2uspto-grants-2015_09