p-Toluenesulfonic acid → 1,1',1''-[2-(4-Bromophenyl)ethene-1,1,2-triyl]tribenzene

HRID 2172375Notes

Reaction equation

HRID 2172375 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(O)[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70944611HCID 70944611, compound

Product 1

HCID 248822081,1',1''-[2-(4-Bromophenyl)ethene-1,1,2-triyl]tribenzeneYield 82.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was prepared following previously published procedures. See M. Banerjee, J. Org. Chem, 2007, 72, 8054. 1-(4-Bromophenyl)-1,2,2-triphenylethanol (5) was obtained as an intermediate in the reaction as a white solid, whose dehydration was carried out in toluene in the presence of TsOH. After being washed by hexane, the crude product was purified on a silica-gel column using petroleum ether as an eluent. A white solid was obtained in 82.1% yield.

Workup

  1. customThis compound was prepared
  2. washAfter being washed by hexane
  3. customthe crude product was purified on a silica-gel column
  4. customA white solid was obtained in 82.1% yield

Sources & evidence

ORD record
ord-47d8b454e917490e8df4b104b92d1fda
Source dataset
uspto-grants-2015_06
Patent number
US09051598B2

Reaction notes

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