Potassium Carbonate → 6-Chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 493214

Reaktionsgleichung

Reaktionsgleichung von HRID 493214
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>CS(C)=O>[CH3:24][O:23][C:19]([C:20]1[S:21][C:4]2[CH:3]=[C:2]([Cl:1])[C:9]([O:10][CH3:11])=[CH:8][C:5]=2[CH:6]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 149282684-Chloro-2-fluoro-5-methoxybenzaldehyde

Produkt 1

HCID 688807806-Chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 4-chloro-2-fluoro-5-methoxybenzaldehyde (0.821 g, 4.35 mmol) in 8.7 mL of DMSO were successively added K2CO3 (1.81 g, 3 eq.) and methyl thioglycolate (0.474 mL, 1.2 eq.), and the mixture was vigorously stirred at 50° C. for 2 h. After cooling, the reaction mixture was poured onto crashed ice/HCl, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated. Flash chromatography (SiO2, hexane/AcOEt=85/15), followed by crystallization from heptane/AcOEt, yielded 0.300 g of the title compound as off-white solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured
  3. extractiontwofold extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customFlash chromatography (SiO2, hexane/AcOEt=85/15), followed by crystallization from heptane/AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-cd34385ba4f74eed82e17c07a4fda942
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534788B2

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