Potassium Carbonate → 5-(4-(Trifluoromethyl)phenyl)thiophene-2-carbaldehyde

HRID 1675306

Reaktionsgleichung

Reaktionsgleichung von HRID 1675306
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 784285-Bromothiophene-2-carbaldehydeHCID 27343894-(Trifluoromethyl)phenylboronic acid

Produkt 1

HCID 46748195-(4-(Trifluoromethyl)phenyl)thiophene-2-carbaldehydeAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 5-bromothiophene-2-carboxaldehyde 60.1 (1.03 g, 5.4 mmol), 4-(trifluoromethyl)benzeneboronic acid 61.1 (2.05 g, 10.9 mmol), K2CO3 (2.24 g, 16.2 mmol), and Pd(PPh3)4 (0.60 g, 0.54 mmol) in toluene (15 mL) was stirred for 5 Hours at 95° C. The mixture was cooled to room temperature, filtered through a pad of silica gel (EtOAc), and concentrated. The crude product was chromatographed on silica gel (0-30% EtOAc/hexane) to afford 61.2 (0.87 g, 63%) as off-white crystals. 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 7.78 (m, 3H), 7.70 (d, 2H), 7.48 (d, 1H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of silica gel (EtOAc)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (0-30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4654cd8c00724fb1a7dfcd410ee21c16
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003648B2

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