Dimethylformamide → Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 589281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589281
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:11][C:10]([F:13])([F:12])[C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:15]([C:14]([O:18][CH3:19])=[O:17])[S:16][C:2]=2[CH:9]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 18526202Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylateAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

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 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.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with tert-butyl methyl ether 3 times
  3. washThe combined organic layer was washed with water
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0247623088074d76875e4ab95f35e7c3
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09232792B2

Notizen zur Reaktion

Wird geladen…