Potassium Carbonate → Methyl 5-phenylthiophene-3-carboxylate

HRID 915692

Reaktionsgleichung

Reaktionsgleichung von HRID 915692
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](Br)[S:7][CH:6]=1)=[O:4].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:7][CH:6]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 45873035Methyl 5-bromothiophene-3-carboxylate

Produkt 1

HCID 819151Methyl 5-phenylthiophene-3-carboxylateAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Prepare a mixture of 5-bromo-thiophene-3-carboxylic acid methyl ester (1.86 g, 8.41 mmol), phenylboronic acid (2.05 g, 16.83 mmol), and 1 M aqueous potassium carbonate (12.5 mL, 25.23 mmol) in 1,2-dimethoxyethane (70 mL) and purge with nitrogen for 20 minutes. Add Pd(PPh3)4 (485 mg, 0.42 mmol) and again purge the mixture with nitrogen for 10 minutes. Heat to 80° C. for 24 hours. Evaporate the solvent and redissolve the residue in ethyl acetate. Extract the aqueous phase with ethyl acetate (2×20 mL), wash the combined organic phases brine (40 mL), dry (magnesium sulfate), filter and concentrate. Perform flash chromatography on silica-gel eluting with 10:1 hexane/ethyl acetate to afford 947 mg of 5-phenylthiophene-3-carboxylic acid methyl ester as a white solid. MS: m/e=219 [MH+].

Aufarbeitung

  1. customPrepare
  2. custompurge with nitrogen for 20 minutes
  3. customEvaporate the solvent
  4. dissolutionredissolve the residue in ethyl acetate
  5. extractionExtract the aqueous phase with ethyl acetate (2×20 mL)
  6. washwash the combined organic phases brine (40 mL)
  7. dry with materialdry (magnesium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate
  10. washPerform flash chromatography on silica-gel eluting with 10:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-372d810bc8534bc5b665097fa0a23c9d
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265246B2

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