Réaction #2358488

ord-02fd34350e7942eba74e894e4aac31d7

Équation de réaction

O=Cc1cccc(C(F)(F)F)c1F
2-fluoro-3-(trifluoromethyl)benzaldehyde
COC(=O)CS
methyl thioglycolate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
DMF
COC(=O)c1cc2cccc(C(F)(F)F)c2s1
methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate
Rendement 89.9%

Solvants

Conditions de réaction

Température
60°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
    Concentrationand then concentrated under reduced pressure

Mode opératoire

A mixture of 1.10 g of 2-fluoro-3-(trifluoromethyl)benzaldehyde, 663 mg of methyl thioglycolate, 1.03 g of potassium carbonate and 15 ml of DMF was stirred at 60° 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 1.34 g of methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (the present compound 4).

Source

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