Reaktion #2358487

ord-1d6e21acf49c416984f75fc425db3b8a

Reaktionsgleichung

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
Ausbeute 35.4%

Lösungsmittel

Reaktionsbedingungen

Temperatur
130°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 1.00 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).

Quelle

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