Toluene → Anthracene

HRID 2179860Notes

Reaction equation

HRID 2179860 reaction equation
C1C2C(=CC=C([C:11]3[C:12]4[C:17]([C:18](Br)=[C:19]5[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]5)=[CH:16][CH:15]=[CH:14][CH:13]=4)C=2)C=CC=1C1C=CC2C(=CC=CC=2)C=1.C1(C2C=CC=CC=2)C(B(O)O)=CC=CC=1.P([O-])([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.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O.C(O)C>[CH:13]1[C:12]2[C:17](=[CH:18][C:19]3[C:24]([CH:11]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 4589187Biphenyl-2-boronic acidHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

Product 1

HCID 8418AnthraceneYield 85.7%

Reagents, catalysts & solvents 4

HCID 75806TricyclohexylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, p-biphenylboronic acid (0.9 g), Pd(dba)2 (0.05 g), tricyclohexyl phosphine (0.05 g), potassium phosphate (1.7 g), and a mixture solvent of toluene and ethanol (15 ml) (toluene/ethanol=4/1 (volume ratio)) were added to a flask and then refluxed for 3 hours. Once the heating is completed, it was cooled to room temperature and added with water. The precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol and purified by silica gel column chromatography (solvent: toluene) and further by active carbon column chromatography (solvent: toluene) to give 9-([1,1′-biphenyl]-4-yl)-10-([2,2′-binaphthalen]-7-yl)]anthracene (0.6 g) as the target compound represented by Formula (1-129). The scheme is shown in the following “Reaction 20”.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with water
  4. custompurified by silica gel column chromatography (solvent: toluene) and further by active carbon column chromatography (solvent: toluene)

Sources & evidence

ORD record
ord-557d0196e940463d8134e2f3902787ac
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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