Toluene → HCID 59524089, compound

HRID 1431036Notes

Reaction equation

HRID 1431036 reaction equation
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3](B(O)O)[CH:2]=1.[Br:20][C:21]1[CH:22]=[C:23](I)[CH:24]=[CH:25][CH:26]=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:20][C:21]1[CH:22]=[C:23]([C:5]2[CH:6]=[CH:7][C:8]3[C:9]4[C:14]([C:15]5[C:16]=3[C:4]=2[CH:3]=[CH:2][CH:1]=5)=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 23088535Fluoranthen-3-ylboronic acid

Product 1

HCID 59524089HCID 59524089, compoundYield 70.4%

Reagents, catalysts & solvents 4

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

Procedure

18.18 g (81.3 mmol) of 3-fluorantheneboronic acid, 22.99 g (81.3 mmol) of 3-bromoiodobenzene, 4.70 g (4.10 mmol) of tetrakis(triphenylphosphine)palladium (0), 80 ml of toluene, 80 ml of dimethoxyethane and 123 g of a 2M sodium carbonate aqueous solution were combined under argon atmosphere, and the mixture was stirred for 8 hours with refluxing and heating. After finishing the reaction, water was added to the reaction mixture, and the mixture was stirred at room temperature for one hour. Methanol was added thereto, and a solid matter was obtained by filtering, and it was refined by silica gel chromatography to obtain 20.43 g (yield: 70.4%) of 3-(3-bromophenyl)fluoranthene.

Workup

  1. temperaturewith refluxing
  2. temperatureheating
  3. additionwas added to the reaction mixture
  4. stirringthe mixture was stirred at room temperature for one hour
  5. customa solid matter was obtained
  6. filtrationby filtering

Sources & evidence

ORD record
ord-016d8bebb6aa43278f73be733fc216d2
Source dataset
uspto-grants-2015_01
Patent number
US08941099B2

Reaction notes

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