Potassium Phosphate, Tribasic → 4-[3-(2-triphen ylenyl)phenyl]-Dibenzothiophene

HRID 71068Notes

Reaction equation

HRID 71068 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:30]=[CH:29][C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[CH:14]=2)[CH:8]=1)(=O)=O.[CH:33]1[C:41]2[C:40]3[CH:42]=[CH:43][CH:44]=[CH:45][C:39]=3[S:38][C:37]=2[C:36](B(O)O)=[CH:35][CH:34]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH:14]1[C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]=2[CH:29]=[CH:30][C:13]=1[C:9]1[CH:8]=[C:7]([C:36]2[C:37]3[S:38][C:39]4[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=4[C:41]=3[CH:33]=[CH:34][CH:35]=2)[CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734329Dibenzothiophene-4-boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 592458333-(Triphenylen-2-yl)phenyl trifluoromethanesulfonate

Product 1

HCID 591476104-[3-(2-triphen ylenyl)phenyl]-DibenzothiopheneYield 88.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4.52 g (10.0 mmol) of 3-(triphenylen-2-yl)phenyl trifluoromethanesulfonate, 3.0 g (13.0 mmol) of 4-dibenzothiopheneboronic acid, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.82 g (2.0 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 12.7 g (60.0 mmol) of K3PO4 and 150 mL of toluene and 15 mL of water were charged in a 250 mL round bottom flask. The reaction mixture was heated up to reflux under nitrogen for overnight. The reaction mixture was cooled and the organic extracts were purified by column chromatography and recrystallization. 4.3 g (88%) of white solid was obtained as product which was confirmed by proton NMR.

Workup

  1. temperatureThe reaction mixture was heated up
  2. temperatureto reflux under nitrogen for overnight
  3. temperatureThe reaction mixture was cooled
  4. customthe organic extracts were purified by column chromatography and recrystallization

Sources & evidence

ORD record
ord-401089687b284c49a0b522a4d4046c85
Source dataset
uspto-grants-2014_09
Patent number
US08822708B2

Reaction notes

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