Sodium Carbonate → Ethyl 2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylate

HRID 1876988

Reaktionsgleichung

Reaktionsgleichung von HRID 1876988
Br[C:2]1[S:6][C:5]([CH2:7][CH3:8])=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.CN(C)C=O.O>[CH2:7]([C:5]1[S:6][C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:15]([F:26])([F:25])[F:14])=[CH:17][CH:18]=2)=[CH:3][C:4]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:8]

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 68515411Ethyl 5-bromo-2-ethylthiophene-3-carboxylate

Produkt 1

HCID 68509779Ethyl 2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of ethyl 5-bromo-2-ethylthiophene-3-carboxylate (4.61 g) synthesized above, 4-(trifluoromethyl)phenylboronic acid (5.00 g), sodium carbonate (3.71 g), water (20 mL) and N,N-dimethylformamide (100 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II).dichloromethane adduct (1.43 g). The reaction mixture was deaerated, and stirred under an argon atmosphere at 80° C. for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio) to give the title compound (5.18 g, 90%) as a white solid.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium hydrogen carbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-f52c1d6ac1374c50bddc299c092e319c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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