Sodium Carbonate → HCID 23067340, compound

HRID 1712228Notes

Reaction equation

HRID 1712228 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:19]=[C:18]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:34]1([C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:41][C:42]2[CH:47]=[CH:46][C:45](OB(O)O)=[CH:44][CH:43]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[C:34]1([C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:41][C:42]2[CH:47]=[CH:46][C:45]([C:2]3[C:3]4[C:8]([C:9]([C:16]5[CH:21]=[C:20]([C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=6)[CH:19]=[C:18]([C:28]6[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=6)[CH:17]=5)=[C:10]5[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]5)=[CH:7][CH:6]=[CH:5][CH:4]=4)=[CH:44][CH:43]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23020580HCID 23020580, compoundHCID 230673259-Bromo-10-[1,1′:3′,1′′-terphenyl]-5′-ylanthracene

Product 1

HCID 23067340HCID 23067340, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under an atmosphere of argon, 9-bromo-10-(3,5-diphenylphenyl)anthracene (3.9 g, 8.0 mmole), 4-(2,2-diphenylvinyl)phenylboric acid (2.7 g, 9.0 mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.16 mmole, 2% Pd) were suspended in toluene (30 ml). To the obtained suspension, a 2M aqueous solution of sodium carbonate (2.9 g, 27 mmole, 3 eq/15 ml) was added, and the resultant mixture was refluxed for 10 hours. An organic layer was separated from the reaction mixture, washed with a saturated aqueous solution of sodium chloride (30 ml) and dried with magnesium sulfate. After the solvent was removed by distillation, a brown solid substance was obtained. The obtained solid substance was purified in accordance with the column chromatography (silica gel/hexane+10% dichloromethane, hexane+20% dichloromethane), and a white solid substance (4.3 g, the yield: 81%) was obtained. The result of examination of the obtained product in accordance with 1H-NMR was as follows:

Workup

  1. customAn organic layer was separated from the reaction mixture
  2. washwashed with a saturated aqueous solution of sodium chloride (30 ml)
  3. dry with materialdried with magnesium sulfate
  4. customAfter the solvent was removed by distillation
  5. customa brown solid substance was obtained
  6. customThe obtained solid substance was purified in accordance with the column chromatography (silica gel/hexane+10% dichloromethane, hexane+20% dichloromethane)
  7. customa white solid substance (4.3 g, the yield: 81%) was obtained
  8. customThe result of examination of the obtained product in accordance with 1H-NMR

Sources & evidence

ORD record
ord-2ccdd0c0c8eb441e8e39d31607289b17
Source dataset
uspto-grants-2010_09
Patent number
US07790892B2

Reaction notes

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