Toluene → 9-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthracene

HRID 2179857Notes

Reaction equation

HRID 2179857 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([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)[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1.[C:36]1([C:42]2[CH:47]=[C:46](B(O)O)[CH:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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.C(O)C>[C:36]1([C:42]2[CH:47]=[C:46]([C:18]3[C:19]4[C:24]([C:11]([C:8]5[CH:9]=[C:10]6[C:5]([CH:4]=[CH:3][C:2]([C:26]7[CH:35]=[CH:34][C:33]8[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=8)[CH:27]=7)=[CH:1]6)=[CH:6][CH:7]=5)=[C:12]5[C:17]=3[CH:16]=[CH:15][CH:14]=[CH:13]5)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 14739363(1~1~,2~1~:2~3~,3~1~-Terphenyl)-2~5~-ylboronic acidHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

Product 1

HCID 867013559-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthraceneYield 41.6%

Reagents, catalysts & solvents 3

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

Procedure

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, [1,1′:3′,1″-terphenyl]-5′-ylboronic acid (1.0 g), Pd(dba)2 (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (1.3 g), and a mixture solvent of toluene and ethanol (20 ml) (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 2 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 crude product was purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene) to give 9-([1,1′:3′,1″-terphenyl]-5′-yl)-10-([2,2′-binaphthalen]-7-yl)anthracene (1.0 g) as the target compound represented by Formula (1-162). The scheme is shown in the following “Reaction 17”.

Workup

  1. temperaturerefluxed for 2 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 crude product
  7. customwas purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene)

Sources & evidence

ORD record
ord-6158255d007747f1a36dd87fc4b56f0b
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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