Toluene → 2-(4-(1,2,2-Triphenylvinyl)phenyl)triphenylene

HRID 871817Notes

Reaction equation

HRID 871817 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:25]=[CH:24][C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:32]1([CH3:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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>[C:32]1([C:38]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:25]=[CH:24][C:23]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[C:10]=4[CH:9]=3)=[CH:4][CH:3]=2)=[C:38]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 581748542-(4-Bromophenyl)triphenylene

Product 1

HCID 866753932-(4-(1,2,2-Triphenylvinyl)phenyl)triphenyleneYield 82%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

The product B (1.25 g, 3.26 mmol), D (1.37 g, 3.58 mmol), potassium carbonate solution (K2CO3(aq), 2.0 M, 8.0 mL), and dried toluene (24 mL) were charged in a two-necked bottle. The bottle was deoxygenated and purged with nitrogen, and the mixture in the bottle was stirred at 60° C. until it was totally dissolved. The nitrogen pressure of the bottle was increased, and Pd(PPh3)4 (381 mg, 0.33 mmol) was rapidly added into the bottle. The reaction was heated to 110° C., and stirred for 48 hours. The resulting was filtered to remove metal. The filtrate was condensed to remove the solvent. The solid was washed by water and methanol, and then sublimated at a temperature of 260° C. to obtain TSTP (1.50 g, yield=82%) as white solid.

Workup

  1. customThe bottle was deoxygenated
  2. custompurged with nitrogen
  3. dissolutionwas totally dissolved
  4. temperatureThe nitrogen pressure of the bottle was increased
  5. temperatureThe reaction was heated to 110° C.
  6. stirringstirred for 48 hours
  7. filtrationThe resulting was filtered
  8. customto remove metal
  9. customcondensed
  10. customto remove the solvent
  11. washThe solid was washed by water and methanol
  12. customsublimated at a temperature of 260° C.
  13. customto obtain TSTP (1.50 g, yield=82%) as white solid

Sources & evidence

ORD record
ord-60257c80087f4d65a7c01d2e724828b9
Source dataset
uspto-grants-2015_03
Patent number
US08974920B2

Reaction notes

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