Chloroform → HCID 67973500, Verbindung

HRID 708308

Reaktionsgleichung

Reaktionsgleichung von HRID 708308
Br[C:2]1[S:3][C:4](Br)=[CH:5][C:6]=1[Br:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[C:20](=[O:23])([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl>C1COCC1.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.CCOC(C)=O>[Br:7][C:6]1[CH:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[S:3][C:2]=1[C:11]1[CH:16]=[CH:15][C:14]([O:23][CH3:20])=[CH:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 76592Thiophene, 2,3,5-tribromo-HCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 67973500HCID 67973500, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

2,3,5-Tribromothiophene (6.42 g, 20 mmol), 4-methoxyphenylboronic acid (6.38 g, 42 mmol) and sodium carbonate (8.5 g, 80 mmol) were stirred in THF/water mixture (125/50 ml) for 90 min at RT under argon flushing. Pd(PPh3)4 (693 mg, 0.6 mmol) was added. The mixture was refluxed for 16 h (TLC), cooled to RT and THF was removed by evaporation. Water was added and aqueous fractions extracted with EtOAc. The organic fractions were combined, solvent removed and the crude product purified by flash chromatography (Silica gel; hexane/chloroform/EtOAc; gradient up to 20% chloroform then 20% EtOAc) to yield 3-bromo-2,5-bis(4-methoxyphenyl)thiophene (4.9 g, 13 mmol, 65%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 16 h (TLC)
  2. customTHF was removed by evaporation
  3. additionWater was added
  4. extractionaqueous fractions extracted with EtOAc
  5. customsolvent removed
  6. customthe crude product purified by flash chromatography (Silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4ad2ec4d58e54e07bd01dbcc2fa5da29
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09176357B2

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