Toluene → 9-([2,2'-Binaphthalen]-7-yl)-10-(phenanthren-9-yl)anthracene

HRID 2179858Notes

Reaction equation

HRID 2179858 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.[CH:36]1[C:49]2[CH:48]=[C:47](B(O)O)[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]=2[CH:39]=[CH:38][CH:37]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]4[C:17]([C:18]([C:48]5[C:49]6[C:40]([C:41]7[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=7[CH:47]=5)=[CH:39][CH:38]=[CH:37][CH:36]=6)=[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

Participants

9

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 117757049-Phenanthracenylboronic acidHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

Product 1

HCID 867013569-([2,2'-Binaphthalen]-7-yl)-10-(phenanthren-9-yl)anthraceneYield 29.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, phenanthren-9-ylboronic acid (1.1 g), palladium acetate (Pd (OAc)2) (0.06 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, manufactured by Aldrich Company) (0.02 g), potassium phosphate (1.7 g), and a mixture solvent (10 ml) of toluene and ethanol (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 10 hours. Once the heating is completed, the reaction solution 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 then purified by silica gel column chromatography (solvent: toluene). Additionally, after re-crystallization with chlorobenzene, 9-([2,2′-binaphthalen]-7-yl)-10-(phenanthren-9-yl)anthracene (0.7 g) was obtained as the target compound represented by Formula (1-164). The scheme is shown in the following “Reaction 18”.

Workup

  1. temperaturerefluxed for 10 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)
  5. customAdditionally, after re-crystallization with chlorobenzene

Sources & evidence

ORD record
ord-6c4ead6cc42042d4b9a3fd711bf19ba1
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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