Ethanol → 4-(7-Phenylbenz[a]anthracen-4-yl)-7-phenylbenz[a]anthracene

HRID 877291

Reaktionsgleichung

Reaktionsgleichung von HRID 877291
BrN1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.[CH:9]1[C:14]2=[C:15]3[C:24](=[CH:25][CH:26]=[C:13]2[C:12]([C:27]2[C:32]4=[CH:33][CH:34]=[C:35]5[C:44]([CH:43]=[C:42]6[C:37]([CH:38]=[CH:39][CH:40]=[CH:41]6)=[CH:36]5)=[C:31]4[CH:30]=[CH:29][CH:28]=2)=[CH:11][CH:10]=1)[CH:23]=[C:22]1[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]1)=[CH:16]3.[CH2:45](O)[CH3:46].[C:48]1(B(O)O)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[C:3]1([C:36]2[C:35]3[C:44]([CH:43]=[C:42]4[C:37]=2[CH:38]=[CH:39][CH:40]=[CH:41]4)=[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([C:12]4[C:13]5=[CH:26][CH:25]=[C:24]6[C:15]([CH:16]=[C:17]7[C:22]([CH:21]=[CH:20][CH:19]=[CH:18]7)=[C:23]6[C:48]6[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=6)=[C:14]5[CH:9]=[CH:10][CH:11]=4)[C:32]2=[CH:33][CH:34]=3)[CH:46]=[CH:45][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 66827Phenylboronic AcidHCID 67184N-bromobutanimideHCID 594125524-(Benz[a]anthracen-4-yl)benz[a]anthracene

Produkt 1

HCID 594127104-(7-Phenylbenz[a]anthracen-4-yl)-7-phenylbenz[a]anthracene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

19.6 g (110 mmol) of N-bromosuccinimide are added in one portion at 100° C. with vigorous stirring to a suspension of 22.7 g (50 mmol) of 4-(benz[a]anthracen-4-yl)benz[a]anthracene in 1000 ml of DMF. The suspension is kept at 100° C. for a further 30 min. and cooled, and 1000 ml of ethanol are then added. The precipitated solid is filtered off with suction, washed three times with 100 ml of ethanol each time and dried in vacuo. The resultant solid is reacted analogously to Example 7 with 15.9 g (130 mmol) of benzeneboronic acid, Recrystallisation five times from DMF (about 6 ml/g); sublimation (p=5×10−5 mbar, T=360° C.). Yield: 21.8 g (36 mmol), 72.0%, purity 99.9% (HPLC), Tg=181.4° C.

Aufarbeitung

  1. temperaturecooled
  2. filtrationThe precipitated solid is filtered off with suction
  3. washwashed three times with 100 ml of ethanol each time
  4. customdried in vacuo
  5. customsublimation (p=5×10−5 mbar, T=360° C.)

Quellen und Nachweise

ORD-Eintrag
ord-52646a4582bf43ba9c9fb5c133992734
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08986852B2

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