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Toluene → HCID 59524089, compound

HRID 1429333
Notes
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Reaction equation

HRID 1429333 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 178418397
HCID 178418397, compound
Catalyst
HCID 887MethanolSolvent
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

In argon atmosphere, a mixture of 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 2 M sodium carbonate aqueous solution was refluxed for 8 h under stirring. After the reaction, 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 20.43 g (yield: 70.4%) of 3-(3-bromophenyl)fluoranthene.

Workup

  1. temperaturewas refluxed for 8 h
  2. customAfter the reaction
  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-a7ee793838e549168e27ab53b905a5c3
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940412B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes