Reaktion #2358486

ord-111c605a61134ec3ae46115e80cc1207

Reaktionsgleichung

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
Ausbeute 56.4%

Lösungsmittel

Reaktionsbedingungen

Temperatur
140°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe reaction mixture was cooled to room temperature
  2. 2
    Extraktionextracted with tert-butyl methyl ether 3 times
  3. 3
    WaschenThe combined organic layer was washed with water
  4. 4
    TrocknenThe mixture was dried over magnesium sulfate
  5. 5
    Einengenconcentrated under reduced pressure

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09119396B2uspto-grants-2015_09