Sodium Carbonate → HCID 57445094, Verbindung

HRID 558144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558144
Br[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[F:11][C:12]1[CH:13]=[CH:14][C:15]([OH:21])=[C:16](B(O)O)[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(Cl)(Cl)Cl.C(O)(C)C.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].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:14]3[CH:13]=[C:12]([F:11])[CH:17]=[CH:16][C:15]=3[OH:21])[C:7]1=2

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 37724765-Fluoro-2-hydroxyphenylboronic acidHCID 120455387-Bromobenzo[b]thiophene

Produkt 1

HCID 57445094HCID 57445094, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 27342152-(Di-tert-butylphosphino)biphenylKatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Combine 7-bromo-benzo[b]thiophene (6.53 g, 30.64 mmol), 5-fluoro-2-hydroxy phenyl boronic acid (4.87 g, 31.26 mmol), Pd(dppf)Cl2 (1.25 g, 1.53 mmol), 2-(di-tert-butylphosphino)biphenyl (0.28 g, 0.92 mmol), sodium carbonate (2 M, 30.64 mL, 61.92 mmol) in dioxane (60 mL, alternative THF) in a flask. Heat the mixture at 100° C. for 2 h. Dilute the mixture with chloroform/IPA (3/1). Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo. Purify the residue by column chromatography (hexane to 10% ethyl acetate in hexane) to give the title compound (6.0 g, 80%) as a yellow solid. MS (ES) m/z 243 [M−1]+.

Aufarbeitung

  1. washWash the solution with aqueous saturated sodium chloride
  2. dry with materialDry over sodium sulfate
  3. concentrationConcentrate the solution in vacuo
  4. customPurify the residue by column chromatography (hexane to 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0e14e4c01f414e0cbfea5db80ad4ef1a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063035B2

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