Sodium Carbonate → 6-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiophene

HRID 2353355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353355
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8](B(O)O)[S:7][C:6]=2[CH:13]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([C:27]([F:30])([F:29])[F:28])[CH:16]=1.[Al].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.[Cl-].[Na+].O.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:17]([C:27]([F:28])([F:30])[F:29])[CH:16]=3)[S:7][C:6]=2[CH:13]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 5359268AluminumHCID 18379633HCID 18379633, VerbindungHCID 53398048(6-Methyl-1-benzothiophen-2-yl)boronic acid

Produkt 1

HCID 684539646-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiopheneAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 15220664Palladium--triphenylphosphane (1/1)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 241BenzeneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a slurry of 6-methyl-benzo[b]thiophene-2-boronic acid (0.19 g, 0.001 mol) in 10 mL of benzene is added 4-bromo-2-trifluoromethyl-biphenyl (0.3 g, 0.001 mol). The reaction flask is then covered with aluminum foil to keep out light. To this is added 58 mg of tetrakis(triphenylphosphine-palladium(0), followed by 1 mL of 2.0N sodium carbonate solution. The biphasic mixture is heated at 85° C. for 3 hours with vigorous stirring. The mixture is cooled to room temperature and 10 mL of brine solution is added. The organic layer is separated, dried and concentrated under vacuo to afford 0.2 g of 6-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-07a190c53f064f4aa5bf0b601c6a79fa
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750021B2

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