1,2,4-Trimethylbenzene → Anthracene

HRID 2179859Notes

Reaction equation

HRID 2179859 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.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C(=CC(=CC=1)C)C)C>CC([O-])=O.CC([O-])=O.[Pd+2].O.C(O)(C)(C)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 5

HCID 72471,2,4-TrimethylbenzeneHCID 62657Potassium Phosphate, TribasicHCID 4589187Biphenyl-2-boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

Product 1

HCID 8418AnthraceneYield 71.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, o-biphenylboronic acid (0.9 g), Pd(OAc)2 (0.03 g), SPhos (manufactured by Aldrich Company) (0.12 g), potassium phosphate (1.7 g), and a mixture solvent of pseudo cumene, t-butyl alcohol, and water (14 ml) (pseudo cumene/t-butyl alcohol/water=10/3/1 (volume ratio)) were added to a flask and refluxed for 8 hours. Once the heating is completed, the reaction solution was cooled to room temperature. The reaction was terminated by adding water. The target compound was extracted with toluene. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel column chromatography (solvent: toluene) and further by active carbon column chromatography (solvent: toluene) to give 9-([1,1′-biphenyl]-2-yl)-10-([2,2′-binaphthalen]-7-yl)]anthracene (0.5 g) as the target compound represented by Formula (1-117). The scheme is shown in the following “Reaction 19”.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe reaction was terminated
  3. additionby adding water
  4. extractionThe target compound was extracted with toluene
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained solid was purified by silica gel column chromatography (solvent: toluene) and further by active carbon column chromatography (solvent: toluene)

Sources & evidence

ORD record
ord-93cabc6d76fd419ea5eb9aabed65c584
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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