N,N'-Dimethylethylenediamine → 4-Bromotriphenylamine

HRID 31958

Reaction equation

HRID 31958 reaction equation
CNCCNC.[C:7]1([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1>[Cu].C1(C)C(C)=CC=CC=1>[CH:17]1[CH:16]=[CH:15][C:14]([N:13]([C:24]2[CH:25]=[CH:26][C:21]([Br:20])=[CH:22][CH:23]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 11487DiphenylamineHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 6428384-BromotriphenylamineYield 70.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7237O-XyleneSolvent

Procedure

N,N′-dimethylethylenediamine 1.76 g was added to diphenylamine 16.9 g, 4-bromoiodobenzene 28.2 g sodium t-butoxide 14.4 g, copper powder 3.81 g and a xylene 100 ml solution, and the mixture was heated and refluxed for 24 hours under argon atmosphere. After cooled down to room temperature, the mixture was filtered to remove an insoluble matter, and the filtrate was concentrated. The residue was refined by silica gel chromatography to obtain 22.7 g of white crystal of 4-bromotriphenylamine.

Workup

  1. temperaturerefluxed for 24 hours under argon atmosphere
  2. filtrationthe mixture was filtered
  3. customto remove an insoluble matter
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-aff8d328fb5246128c3497ee689c6469
Source dataset
uspto-grants-2008_09
Patent number
US07425654B2

Linked notes

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