1,2-Dimethoxyethane → 7-Bromo-2-(9-phenanthrenyl)naphthalene

HRID 1429328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429328
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][C:23](Br)=[CH:24][CH:25]=2)[CH:20]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:20]=[C:21]2[C:26]([CH:25]=[CH:24][C:23]([C:12]3[C:11]4[C:6]([C:5]5[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=5[CH:13]=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[CH:22]2)=[CH:27][CH:28]=1

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 6253552,7-DibromonaphthaleneHCID 117757049-Phenanthracenylboronic acid

Produkt 1

HCID 575400157-Bromo-2-(9-phenanthrenyl)naphthaleneAusbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

In argon atmosphere, a mixture of 18.64 g (83.9 mmol) of 9-phenanthreneboronic acid, 30.00 g (104.9 mmol) of 2,7-dibromonaphthalene, 4.85 g (4.2 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of dimethoxyethane, 200 ml of toluene, and 106 ml of a 2 M sodium carbonate was stirred at a bath temperature of 85° C. for 7 h. The reaction mixture was added with water and extracted with toluene. After washing with water, the organic phase was dried over magnesium sulfate. Then, the toluene was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 12.46 g (yield: 31.0%) of 7-bromo-2-(9-phenanthrenyl)naphthalene.

Aufarbeitung

  1. extractionextracted with toluene
  2. washAfter washing with water
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customThen, the toluene was removed by distillation under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-036d58eace664723946406ef9fdfad22
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940412B2

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