Reacción #2358487

ord-1d6e21acf49c416984f75fc425db3b8a

Ecuación de reacción

O=Cc1c(F)cccc1C(F)(F)F
2-fluoro-6-(trifluoromethyl)benzaldehyde
COC(=O)CS
methyl thioglycolate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
DMF
COC(=O)c1cc2c(C(F)(F)F)cccc2s1
methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate
Rendimiento 35.4%

Disolventes

Condiciones de reacción

Temperatura
130°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 1.00 g of 2-fluoro-6-(trifluoromethyl)benzaldehyde, 633 mg of methyl thioglycolate, 1.21 g of potassium carbonate and 15 ml of DMF was stirred at 130° C. for 2 hours. 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 480 mg of methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (the present compound 3).

Fuente

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