Dichloromethane → 2-(4-Fluorophenyl)thiophene

HRID 1837959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837959
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>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>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)=[CH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 138512-BromothiopheneHCID 2856454-Fluorophenylboronic acid

Produkt 1

HCID 218947832-(4-Fluorophenyl)thiopheneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-bromothiophene (1.0 g, 6.14 mmol) in 1,2-dimethoxyethane (11 mL) was added 4-fluorophenylboronic acid (1.12 g, 7.99 mmol), followed by Pd(PPh3)4 (360 mg, 0.31 mmol) and a 2M Na2CO3 aq. solution (8 mL). The reaction mixture was heated at 80° C. for 4 h, then was poured onto a mixture of ice and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3×20 mL). The organic layers were dried (MgSO4) and concentrated under reduced pressure to yield a yellow oil. The crude product was filtered through a plug of silica with the aid of hexanes to give 4-fluorophenylthiphene (1.04 g, 95%). TLC (hex) Rf=0.40.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto yield a yellow oil
  5. filtrationThe crude product was filtered through a plug of silica with the aid of hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3b10e24587154e11af804fd140284dc0
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784167B2

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