Toluene → 9-([2,2'-Binaphthalen]-7-yl)anthracene

HRID 2179854Notes

Reaction equation

HRID 2179854 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12]C(C3C=CC4C(=CC=CC=4)C=3)=[CH:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH:29]1[C:42]2[C:33](=[CH:34][C:35]3[C:40]([C:41]=2B(O)O)=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:32]=[CH:31][CH:30]=1.[CH:46]1(P(C2CCCCC2)C2CCCCC2)[CH2:51]CC[CH2:48][CH2:47]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:73]1([CH3:79])[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=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].C(O)C>[CH:74]1[C:75]2[C:76](=[CH:51][CH:46]=[C:47]([C:41]3[C:42]4[C:33]([CH:34]=[C:35]5[C:40]=3[CH:39]=[CH:38][CH:37]=[CH:36]5)=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:48]=2)[CH:77]=[CH:78][C:73]=1[C:79]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][CH:7]=[CH:8][CH:9]=2)[CH:14]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 155102139-Anthraceneboronic AcidHCID 86701351[2,2'-Binaphthalen]-7-yl trifluoromethanesulfonate

Product 1

HCID 867013539-([2,2'-Binaphthalen]-7-yl)anthracene

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 702EthanolSolvent

Procedure

Under the nitrogen atmosphere, [2,2′-binaphthalen]-7-yl trifluoromethane sulfonate (16.0 g) as the eighth intermediate compound, anthracen-9-ylboronic acid (13.3 g), Pd(dba)2 (0.7 g), tricyclohexyl phosphine (0.8 g), potassium phosphate (16.9 g), and a mixture solvent (120 ml) of toluene and ethanol (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 2.5 hours. Once the heating is completed, the reaction solution was cooled. Liquid separation was performed by adding water and toluene. Subsequently, the organic layer was distilled off under reduced pressure and the obtained crude product was purified by silica gel column chromatography (solvent: toluene). The solid obtained by distillation of the solvent under reduced pressure was washed with heptane to give 9-([2,2′-binaphthalen]-7-yl)anthracene (10.0 g) as a ninth intermediate compound. The scheme is shown in the following “Reaction 14”.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. temperaturethe reaction solution was cooled
  3. customLiquid separation
  4. additionby adding water and toluene
  5. distillationSubsequently, the organic layer was distilled off under reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (solvent: toluene)
  8. customThe solid obtained by distillation of the solvent under reduced pressure
  9. washwas washed with heptane

Sources & evidence

ORD record
ord-50e4426009d242b784f6160bed1461dd
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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