Nitrogen → 6-Anthracen-9-ylphenanthrene-9-carboxylic acid

HRID 879922

Reaktionsgleichung

Reaktionsgleichung von HRID 879922
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2B(O)O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[C:21]2[C:30](=[CH:31][CH:32]=1)[C:29]([C:33]([OH:35])=[O:34])=[CH:28][C:27]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]2=1.C([O-])([O-])=O.[Na+].[Na+].N#N>C1(C)C=CC=CC=1.CCO.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.CO>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:19]2[CH:20]=[C:21]4[C:30](=[CH:31][CH:32]=2)[C:29]([C:33]([OH:35])=[O:34])=[CH:28][C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]4=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2894646-Bromophenanthrene-9-carboxylic acidHCID 155102139-Anthraceneboronic Acid

Produkt 1

HCID 596294916-Anthracen-9-ylphenanthrene-9-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

32.86 g (148 mmol) of anthracene-9-boronic acid, 37.2 g (124 mmol) of 6-bromophenanthrene-9-carboxylic acid and 220 ml of 2 M Na2CO3 solution are suspended in 1 l of toluene and 1 l of EtOH, the mixture is saturated with N2, 2.9 g (3 mmol) of tetrakis(triphenylphosphine)palladium(0) are added, and the mixture is heated at the boil for 2 h. The mixture is poured into 3 l of a mixture of water/MeOH/6 M HCl 1:1:1, and the beige precipitate is filtered off with suction, washed with water, EtOH and toluene and dried. The content of product according to 1H-NMR is about 96% with an overall yield of 38.5 g (78%).

Aufarbeitung

  1. additionare added
  2. temperaturethe mixture is heated at the boil for 2 h
  3. filtrationthe beige precipitate is filtered off with suction
  4. washwashed with water, EtOH and toluene
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3ebbd0e323584a6d9b3fabd3922fed03
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993123B2

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