Toluene → HCID 58569608, compound

HRID 1429334Notes

Reaction equation

HRID 1429334 reaction equation
[CH:1]1[C:18]2[CH:17]=[CH:16][C:15]3[C:6](=[CH:7][C:8](B(O)O)=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:22][C:23]1[CH:24]=[C:25](I)[CH:26]=[CH:27][CH:28]=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:22][C:23]1[CH:24]=[C:25]([C:17]2[CH:16]=[C:15]3[C:6](=[C:5]4[C:18]=2[CH:1]=[CH:2][CH:3]=[CH:4]4)[CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]3=2)[CH:26]=[CH:27][CH:28]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 11818111HCID 11818111, compound

Product 1

HCID 58569608HCID 58569608, compoundYield 28.4%

Reagents, catalysts & solvents 4

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

Procedure

In argon atmosphere, a mixture of 5.00 g (18.37 mmol) of 6-chryseneboronic acid, 5.20 g (18.37 mmol) of 3-bromoiodobenzene, 1.06 g (0.92 mmol) of tetrakis(triphenylphosphine)palladium (0), 30 ml of toluene, 30 ml of dimethoxyethane, and 27.6 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 2.00 g (yield: 28.4%) of 6-(3-bromophenyl)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-d3745d73a2bf46298212e98bc92386c4
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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