Potassium Phosphate, Tribasic → 2,8-Di(triphenylen-2-yl)dibenzothiophene

HRID 1748951Notes

Reaction equation

HRID 1748951 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]=3[CH:10]=2)O1.Br[C:29]1[CH:42]=[CH:41][C:32]2[S:33][C:34]3[CH:39]=[CH:38][C:37](Br)=[CH:36][C:35]=3[C:31]=2[CH:30]=1.C1(P(C2CCCCC2)[C:50]2[CH:55]=[CH:54]C=C[C:51]=2[C:56]2[C:61](OC)=[CH:60][CH:59]=[CH:58][C:57]=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:19]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:24](=[CH:25][CH:26]=[CH:9][CH:10]=3)[C:23]=2[CH:22]=[CH:21][C:20]=1[C:29]1[CH:42]=[CH:41][C:32]2[S:33][C:34]3[CH:39]=[CH:38][C:37]([C:9]4[CH:26]=[CH:25][C:24]5[C:57]6[C:56](=[CH:61][CH:60]=[CH:59][CH:58]=6)[C:51]6[C:12](=[CH:13][CH:54]=[CH:55][CH:50]=6)[C:11]=5[CH:10]=4)=[CH:36][C:35]=3[C:31]=2[CH:30]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6311202,8-DibromodibenzothiopheneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 587694494,4,5,5-Tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 594892382,8-Di(triphenylen-2-yl)dibenzothiopheneYield 94%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2.25 g (6.3 mmol) of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane, 0.92 g (2.7 mmol) of 2,8-dibromodibenzothiophene, 0.12 g (0.14 mmol) of Pd2(dba)3, 0.22 g (0.53 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 3.4 g (16.0 mmol) of K3PO4, 100 mL of toluene and 10 mL of water were charged in a 250 mL round bottom flask. The reaction mixture was purged with nitrogen for 20 min and then heated up to reflux for overnight with stirring. The reaction mixture was cooled and filtered. The white solid was washed with methanol 3 times (3×100 mL) and methylene chloride (2×100 mL). 1.6 g of (94% yield) solid was obtained as the product which was further purified by recrystallization with toluene and sublimation. The product was confirmed by solid probe MS.

Workup

  1. customThe reaction mixture was purged with nitrogen for 20 min
  2. temperatureheated up
  3. temperatureto reflux for overnight
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. washThe white solid was washed with methanol 3 times (3×100 mL) and methylene chloride (2×100 mL)

Sources & evidence

ORD record
ord-aaaf0e4c09c74dda8137c5aaae74322e
Source dataset
uspto-grants-2015_10
Patent number
US09153786B2

Reaction notes

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