Toluene → 4-(2-Triphenylenyl)dibenzothiophene

HRID 1748949Notes

Reaction equation

HRID 1748949 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25][C:24]=2[C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].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.O>[CH:3]1[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][C:2]=1[C:32]1[C:26]2[S:25][C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:28]=3[C:27]=2[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 2734329Dibenzothiophene-4-boronic acidHCID 183811742-Bromotriphenylene

Product 1

HCID 594892474-(2-Triphenylenyl)dibenzothiopheneYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

4.4 g (14.6 mmol) of 2-bromotriphenylene, 4.0 g (17.5 mmol) of 4-dibenzothiopheneboronic acid, 0.51 g (0.44 mmol) of tetrakistriphenylphosphinepalladium, and 4.0 g (43.4 mmol) of potassium carbonate were charged in a 250 mL round bottom flask with solvent 90 mL of toluene and 10 mL of water. The reaction mixture was purged with nitrogen for 30 min and then was heated up to reflux for overnight under nitrogen with stirring. The reaction mixture was cooled and the organic extracts were purified by column chromatography and recrystallization with toluene. 5.1 g (86%) of white solid was obtained as the product which was confirmed by proton NMR.

Workup

  1. customThe reaction mixture was purged with nitrogen for 30 min
  2. temperaturewas heated up
  3. temperatureto reflux for overnight under nitrogen
  4. temperatureThe reaction mixture was cooled
  5. customthe organic extracts were purified by column chromatography and recrystallization with toluene

Sources & evidence

ORD record
ord-d82432693f5348bca5b804a083f3d703
Source dataset
uspto-grants-2015_10
Patent number
US09153786B2

Reaction notes

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