Potassium trifluoroacetate → Ethyl 5-trifluoromethyl-6-methoxybenzo[b]thiophene-3-carboxylate

HRID 581983

Reaktionsgleichung

Reaktionsgleichung von HRID 581983
Br[C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]=2[CH:3]=1.[F:18][C:19]([F:24])([F:23])C([O-])=O.[K+]>CN(C)C=O.C1(C)C=CC=CC=1.[Cu]I>[F:18][C:19]([F:24])([F:23])[C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]=2[CH:3]=1

Komponenten

6

Edukt 2

HCID 23662811Potassium trifluoroacetateHCID 53817228Ethyl 5-bromo-6-methoxybenzo[b]thiophene-3-carboxylate

Produkt 1

HCID 53925736Ethyl 5-trifluoromethyl-6-methoxybenzo[b]thiophene-3-carboxylateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl-5-bromo-6-methoxybenzo[b]thiophene-3-carboxylate (D4) (0.81 g, 3 mmoles) in dry dimethylformamide (20 ml) and toluene (10 ml) was treated with potassium trifluoroacetate (0.78 g, 6 mmoles) and copper (I) iodide (0.98 g, 6 mmoles). The mixture was heated under reflux for 1 hr using a Dean-Stark trap to collect the toluene. The mixture was cooled and poured into water (150 ml) and extracted with diethyl ether. The resulting emulsion was filtered through kieselguhr. The combined organic extracts were washed several times with water then dried (Na2SO4). Flash chromatography on TLC silica gel eluting with dichloromethane/60-80 petrol ether 1:1 gave the title compound (D6) (0.5 g, 64%)

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customto collect the toluene
  4. temperatureThe mixture was cooled
  5. additionpoured into water (150 ml)
  6. extractionextracted with diethyl ether
  7. filtrationThe resulting emulsion was filtered through kieselguhr
  8. washThe combined organic extracts were washed several times with water
  9. dry with materialthen dried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-8f7003c0a7184667a2fb0c32d57f3ebe
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922733

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