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

HRID 889802Notes

Reaction equation

HRID 889802 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0778d2c945ff4e1386f6f60b3961e346
Source dataset
uspto-grants-2006_02
Patent number
US06994941B2

Reaction notes

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