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

HRID 1776083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776083
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 2 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the mixture was extracted with tert-butyl methyl ether three times. The combined organic layers were washed with water and saturated saline, and dried over magnesium sulfate, then, concentrated under reduced pressure, to obtain 848 mg of methyl 6-(trifluoromethyl)benzo[b]thiophene-2carboxylate (present condensed ring compound 2).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe mixture was extracted with tert-butyl methyl ether three times
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-be41325f571742ba84d855f4424e8a88
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265251B2

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