Réaction #2358487

ord-1d6e21acf49c416984f75fc425db3b8a

Équation de réaction

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
Rendement 35.4%

Solvants

Conditions de réaction

Température
130°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 1.00 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).

Source

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