Cesium carbonate → HCID 58526509, Verbindung

HRID 1190243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190243
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([C:23]2[N:28]=[C:27]([C:29]3[CH:30]=[C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:32]=[C:33]([Cl:35])[CH:34]=3)[N:26]=[C:25]([C:42]3[CH:47]=[C:46](Br)[CH:45]=[C:44](Br)[CH:43]=3)[N:24]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.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>[Cl:10][C:11]1[CH:12]=[C:13]([C:23]2[N:28]=[C:27]([C:29]3[CH:30]=[C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:32]=[C:33]([Cl:35])[CH:34]=3)[N:26]=[C:25]([C:42]3[CH:47]=[C:46]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:45]=[C:44]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:43]=3)[N:24]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 58526512HCID 58526512, Verbindung

Produkt 1

HCID 58526509HCID 58526509, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a stream of argon, phenylboronic acid (904 mg), 4,6-bis(5-chlorobiphenyl-3-yl)-2-(3,5-dibromophenyl)-1,3,5-triazine (1.70 g), cesium carbonate (2.41 g) and tetrakis(triphenylphosphine)palladium (114 mg) were suspended in tetrahydrofuran (80 mL), and the mixture was refluxed for 18 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the reaction mixture, and the solid precipitate was recovered by filtration, and purified by silica gel chromatography using a chloroform/hexane (1:2 to 1:0) mixed liquid as a developing solvent to give 1.42 g of the target 2,4-bis(5-chlorobiphenyl-3-yl)-6-[(1,1′:3′,1″)-terphenyl-5′-yl]-1,3,5-triazine as a yellowish white powder (yield: 84%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 18 hours
  2. waitThe reaction mixture was left
  3. customto stand at room temperature
  4. distillationlow-boiling ingredients were distilled away under a reduced pressure
  5. additionMethanol was added to the reaction mixture
  6. filtrationthe solid precipitate was recovered by filtration
  7. custompurified by silica gel chromatography
  8. additionmixed liquid as a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-b07acd08840e417aacec9ce5a6a1d20c
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674091B2

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