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4-Bromo-4'-iodobiphenyl → N4'-(4'-bromobiphenyl-4-yl)-N4,N4'-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4'-diamine

HRID 889802
Notizen
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Reaktionsgleichung

Reaktionsgleichung von HRID 889802
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=3[CH3:30])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.[Br:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][C:48](I)=[CH:47][CH:46]=2)=[CH:41][CH:40]=1>[Cu].ClC1C=CC=CC=1Cl>[Br:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][C:48]([N:22]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=3[CH3:30])[C:19]3[CH:20]=[CH:21][C:16]([C:13]4[CH:12]=[CH:11][C:10]([N:9]([C:3]5[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=5[CH3:1])[C:31]5[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=5)=[CH:15][CH:14]=4)=[CH:17][CH:18]=3)=[CH:47][CH:46]=2)=[CH:41][CH:40]=1
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Komponenten

5

Edukt 2

HCID 109044524-Bromo-4'-iodobiphenylHCID 86597908N4,N4'-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4'-diamine

Produkt 1

HCID 69525885N4'-(4'-bromobiphenyl-4-yl)-N4,N4'-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4'-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 7239
1,2-Dichlorobenzene
Lösungsmittel

Versuchsvorschrift

Into a 2 liter three-necked reaction vessel fitted with an air-cooling tube and a mechanical stirrer, 48.3 g (0.1 mol) of N4,N4′-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4′-diamine, 39.5 g (0.11 mol) of 4′-bromo-4-iodobiphenyl, 20 g of copper powder and 200 mL of o-dichlorobenzene were introduced and heated for 12 hours in an oil bath. After the reaction was completed, the reaction mixture was left to cool to room temperature, followed by removing solid matter by filtration, and thereafter extraction with toluene/water. Then, the solvent was distilled away from the organic layer under reduced pressure, followed by purification with a silica gel column (developer solvent: hexane/toluene=2:1) to give the desired N4′-(4′-bromobiphenyl-4-yl)-N4,N4′-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4′-diamine. The compound obtained was in a yield of 45.0 g corresponding to 63%. The compound obtained was measured with the same elementary analyzer as the above.

Aufarbeitung

  1. customInto a 2 liter three-necked reaction vessel fitted with an air-cooling tube and a mechanical stirrer
  2. temperatureheated for 12 hours in an oil bath
  3. waitthe reaction mixture was left
  4. customby removing solid matter
  5. filtrationby filtration
  6. extractionextraction with toluene/water
  7. distillationThen, the solvent was distilled away from the organic layer under reduced pressure
  8. customfollowed by purification with a silica gel column (developer solvent: hexane/toluene=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0778d2c945ff4e1386f6f60b3961e346
Quelldatensatz
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06994941B2

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