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Thiophene, 2,3,5-tribromo- → 3-Bromo-2,5-bis(4-(tert-butyl)phenyl)thiophene

HRID 708306
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 708306
O.C(=O)([O-])[O-].[Na+].[Na+].[C:8]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].Br[C:22]1[S:23][C:24](Br)=[CH:25][C:26]=1[Br:27]>O.C1COCC1.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>[Br:27][C:26]1[CH:25]=[C:24]([C:15]2[CH:16]=[CH:17][C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:13][CH:14]=2)[S:23][C:22]=1[C:15]1[CH:16]=[CH:17][C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 76592Thiophene, 2,3,5-tribromo-HCID 27343204-tert-Butylphenylboronic acidHCID 2735133Sodium Carbonate Monohydrate

Produkt 1

HCID 679735833-Bromo-2,5-bis(4-(tert-butyl)phenyl)thiopheneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium carbonate monohydrate (58.0 g, 468 mmol) was dissolved in water (500 mL) and a solution of 4-(tert-butyl)-phenylboronic acid (40.0 g) and 2,3,5-tribromothiophene (30.0 g, 94 mmol) in THF (500 mL) was added, and deoxygenated by bubbling with argon. Pd(PPh3)4 (5.0 g, 4.30 mmol) was added and the mixture refluxed for 24 h. The mixture was cooled and the aqueous phase separated and extracted with EtOAc. Organic fractions were combined washed with water (500 mL) and dried over MgSO4. The solvent was evaporated and the crude product washed in MeOH, filtered and dried overnight to afford a light yellow, powdery solid (35.46 g, 89%).

Aufarbeitung

  1. customdeoxygenated
  2. customby bubbling with argon
  3. temperaturethe mixture refluxed for 24 h
  4. temperatureThe mixture was cooled
  5. customthe aqueous phase separated
  6. extractionextracted with EtOAc
  7. washOrganic fractions were combined washed with water (500 mL)
  8. dry with materialdried over MgSO4
  9. customThe solvent was evaporated
  10. washthe crude product washed in MeOH
  11. filtrationfiltered
  12. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-1995a93b609848b0a366d2f4f7a5bf92
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09176357B2

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