Dichloromethane → 1-Methylpyrene

HRID 1914409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914409
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:18]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>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].O.CN(C)C=O>[CH3:18][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 1596271-BromopyreneHCID 574072Trimethylboroxine

Produkt 1

HCID 169321-MethylpyreneAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixed solution of 7 g of 1-bromopyrene, 6 g of trimethylboroxin, 12 g of cesium carbonate, 2 g of PdCl2(dppf).CH2Cl2, 80 ml of dimethylformamide and 8 ml of distilled water was heated and stirred under a nitrogen gas stream at 80° C. for 7 hours. The solution was cooled to room temperature and 50 ml of water was poured into the solution, followed by filtration. The resulting solid was purified by silica gel column chromatography and then vacuum-dried to obtain 4.4 g of 1-methylpyrene.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. customThe resulting solid was purified by silica gel column chromatography
  4. customvacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-fff84b02595d430f86599072f696d4b5
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08610345B2

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