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Toluene → HCID 59489285, compound

HRID 385309
Notes
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Reaction equation

HRID 385309 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:30]=[CH:29][C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[CH:14]=2)[CH:8]=1)(=O)=O.[CH3:33][O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[CH3:33][O:34][C:35]1[CH:36]=[C:37]([C:11]2[CH:12]=[CH:7][CH:8]=[C:9]([C:13]3[CH:30]=[CH:29][C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15]=4[CH:14]=3)[CH:10]=2)[CH:38]=[CH:39][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 592458333-(Triphenylen-2-yl)phenyl trifluoromethanesulfonate

Product 1

HCID 59489285HCID 59489285, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalyst
HCID 962WaterSolvent

Procedure

12.9 g (28.5 mmol) 3-(triphenylen-2-yl)phenyl trifluoromethanesulfonate, 6.5 g (42.8 mmol) 3-methoxyphenylboronic acid, 0.47 g (1.1 mmol) 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) and 18.2 g (85.5 mmol) potassium phosphate tribasic (K3PO4) were weighed in a round bottom flask. 150 mL toluene and 80 mL water were added to the flask as solvent. The solution was purged with nitrogen and 0.26 g (0.28 mmol) of tris(dibenzylideneacetone)dipalladium (0) [Pd2(dba)3] was added. The solution was heated to reflux for twelve hours. Upon cooling, the organic layer was separated, and dried with MgSO4. The product was readily separated by column chromatography using hexane/dichloromethane as eluent (1/0 gradient to 3/2). The solvent was removed by rotary evaporation resulting in 11.7 g (28 mmol) of the product, 2-(3′-methoxybiphenyl-3-yl)triphonylene.

Workup

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureto reflux for twelve hours
  4. temperatureUpon cooling
  5. customthe organic layer was separated
  6. dry with materialdried with MgSO4
  7. customThe product was readily separated by column chromatography
  8. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-543217797b774adf9fa7e0b7986b10ff
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367850B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes