Reacción #2358486

ord-111c605a61134ec3ae46115e80cc1207

Ecuación de reacción

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
Rendimiento 56.4%

Disolventes

Condiciones de reacción

Temperatura
140°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe reaction mixture was cooled to room temperature
  2. 2
    Extracciónextracted with tert-butyl methyl ether 3 times
  3. 3
    LavadoThe combined organic layer was washed with water
  4. 4
    SecadoThe mixture was dried over magnesium sulfate
  5. 5
    Concentraciónconcentrated under reduced pressure

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09119396B2uspto-grants-2015_09