Tris(4-bromophenyl)amine → 4-(Thiophen-2-yl)-N,N-bis(4-(thiophen-2-yl)phenyl)aniline

HRID 14352Notes

Reaction equation

HRID 14352 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)CCC>C1(C)C=CC=CC=1.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>[S:29]1[CH:30]=[CH:31][CH:32]=[C:28]1[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:30]3[S:29][CH:28]=[CH:32][CH:31]=3)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 258027Tris(4-bromophenyl)amineHCID 27793732-(Tri-n-butylstannyl)thiophene

Product 1

HCID 153154284-(Thiophen-2-yl)-N,N-bis(4-(thiophen-2-yl)phenyl)anilineYield 85%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

First, 1 g (2 mmol) of tris(4-bromophenyl)amine (Aldrich) was dissolved in 100 ml of toluene, and then 2.9 ml (4.5 eq.) of 2-tributylstannylthiophene and 27 mg (1.1%) of Pd(PPh3)4 were added thereto. The mixture was refluxed under a nitrogen atmosphere for 12 hours. The reaction mixture was allowed to cool to room temperature, washed with brine twice, and dried over MgSO4. After the solvent was evaporated, the obtained residue was washed with petroleum ether (PE), and dried, affording 0.87 g (yield: 85%) of tris[4-(2-thienyl)phenyl]amine as a pale yellow solid.

Workup

  1. temperatureThe mixture was refluxed under a nitrogen atmosphere for 12 hours
  2. washwashed with brine twice
  3. dry with materialdried over MgSO4
  4. customAfter the solvent was evaporated
  5. washthe obtained residue was washed with petroleum ether (PE)
  6. customdried

Sources & evidence

ORD record
ord-7c16fafe58124208947e5b9c94c8c2d7
Source dataset
uspto-grants-2010_06
Patent number
US07731796B2

Reaction notes

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