Nitrogen → 6-(10-Naphth-2-ylanthracen-9-yl)phenanthrene-9-carboxylic acid

HRID 879920

Reaktionsgleichung

Reaktionsgleichung von HRID 879920
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](B(O)O)=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[CH:16]2.Br[C:29]1[CH:30]=[C:31]2[C:40](=[CH:41][CH:42]=1)[C:39]([C:43]([OH:45])=[O:44])=[CH:38][C:37]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]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:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:29]2[CH:30]=[C:31]3[C:40](=[CH:41][CH:42]=2)[C:39]([C:43]([OH:45])=[O:44])=[CH:38][C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]3=2)=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[CH:16]2

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2894646-Bromophenanthrene-9-carboxylic acidHCID 2308855610-(2-Naphthyl)anthracene-9-boronic Acid

Produkt 1

HCID 596294876-(10-Naphth-2-ylanthracen-9-yl)phenanthrene-9-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

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

Versuchsvorschrift

51.6 g (148 mmol) of 10-naphth-2-ylanthracen-9-ylboronic 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 suspension 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 94% with an overall yield of 58 g (90%).

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-e530008fa1074bcfa2ec92f4b4074ac9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993123B2

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