Toluene → HCID 59489238, compound

HRID 71069Notes

Reaction equation

HRID 71069 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][CH:53]=[CH:52][C:51]=2[C:56]2C(OC)=[CH:60][CH:59]=[CH:58][C:57]=2OC)CCCCC1.[C:72]1([CH3:78])[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[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:74]4[CH:75]=[CH:76][C:77]5[C:52]6[C:51](=[CH:50][CH:55]=[CH:54][CH:53]=6)[C:56]6[C:78](=[CH:60][CH:59]=[CH:58][CH:57]=6)[C:72]=5[CH:73]=4)=[CH:36][C:35]=3[C:31]=2[CH:30]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6311202,8-DibromodibenzothiopheneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 587694494,4,5,5-TetraMethyl-2-(3-triphenylen-2-yl-phenyl)-[1,3,2]dioxaborolane

Product 1

HCID 59489238HCID 59489238, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

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 K3PO4100, 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-5da14525b29e488182d2a090fd4f6ed0
Source dataset
uspto-grants-2014_09
Patent number
US08822708B2

Reaction notes

Loading…