Potassium Carbonate → (E)-2-(4-Styrylphenyl)triphenylene

HRID 871816Notes

Reaction equation

HRID 871816 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.[CH:26](/B(O)O)=[CH:27]\[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1>[CH:26](/[C:2]1[CH:3]=[CH:4][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:6][CH:7]=1)=[CH:27]\[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 581748542-(4-Bromophenyl)triphenylene

Product 1

HCID 86675392(E)-2-(4-Styrylphenyl)triphenyleneYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The product B (400 mg, 1.04 mmol) or B1, (E)-styrylboronic acid (185 mg, 1.25 mmol), potassium carbonate solution (2.0 M, 4.0 mL) and dried toluene (12 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 (120 mg, 0.1 mmol) was rapidly added into the bottle. The reaction was heated to 110° C., and stirred for 48 hours. The resulting was cooled to room temperature to precipitate a solid, and the solid was collected by filtering. The solid was washed by water and methanol, and then sublimated at a temperature of 230° C. to obtain TSP (317 mg, yield=75%) 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. temperatureThe resulting was cooled to room temperature
  8. customto precipitate a solid
  9. customthe solid was collected
  10. filtrationby filtering
  11. washThe solid was washed by water and methanol
  12. customsublimated at a temperature of 230° C.
  13. customto obtain TSP (317 mg, yield=75%) as white solid

Sources & evidence

ORD record
ord-30ee0fc6fcad48279e8e5d32e6e8dd03
Source dataset
uspto-grants-2015_03
Patent number
US08974920B2

Reaction notes

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