Toluene → HCID 59524129, compound

HRID 1429335Notes

Reaction equation

HRID 1429335 reaction equation
[CH:1]1[C:6]2[C:7]3[C:16]([C:17]4[C:22]([C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][C:14](B(O)O)=[C:13]1[C:8]=3[CH:9]=[CH:10][CH:11]=[CH:12]1.[Br:26][C:27]1[CH:28]=[C:29](I)[CH:30]=[CH:31][CH:32]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.CO.O.C(COC)OC>[Br:26][C:27]1[CH:28]=[C:29]([C:14]2[CH:15]=[C:16]3[C:7](=[C:8]4[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]4)[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:22]2[C:17]3=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:30]=[CH:31][CH:32]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 59582968HCID 59582968, compound

Product 1

HCID 59524129HCID 59524129, compoundYield 34.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In argon atmosphere, a mixture of 5.00 g (15.52 mmol) of 10-benzo[g]chryseneboronic acid, 4.39 g (15.52 mmol) of 3-bromoiodobenzene, 0.90 g (0.78 mmol) of tetrakis(triphenylphosphine)palladium (0), 30 ml of toluene, 30 ml of dimethoxyethane, and 23.28 g of a 2 M sodium carbonate aqueous solution was refluxed for 8 h under stirring and left standing overnight. The reaction mixture was added with water and stirred at room temperature for one hour. After adding methanol, the solid matter was collected by filtration and purified by silica gel chromatography to obtain 2.30 g (yield: 34.2%) of 10-(3-bromophenyl)benzo[g]chrysene.

Workup

  1. temperaturewas refluxed for 8 h
  2. waitleft
  3. stirringstirred at room temperature for one hour
  4. filtrationthe solid matter was collected by filtration
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-49ecf28d0d7445c3ada6236eac75d463
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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