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1,2-Dimethoxyethane → 1-(4-Chlorophenyl)-3-(9,9-dimethylfluoren-2-yl)-7-t-butylpyrene

HRID 1404891
Notes
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Reaction equation

HRID 1404891 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:3]=1.[CH3:29][C:30]1([CH3:46])[C:42]2[CH:41]=[C:40](B(O)O)[CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:4]2[C:5]3[C:16]4=[C:17]5[C:8](=[CH:7][CH:6]=3)[CH:9]=[C:10]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=[C:12]5[CH:13]=[CH:14][C:15]4=[C:2]([C:40]3[CH:39]=[CH:38][C:37]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:30]([CH3:29])([CH3:46])[C:42]=4[CH:41]=3)[CH:3]=2)=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 22348454(9,9-Dimethyl-9H-fluoren-2-yl)boronic acidHCID 866607561-Bromo-7-t-butyl-3-(4-chlorophenyl)pyrene

Product 1

HCID 866607591-(4-Chlorophenyl)-3-(9,9-dimethylfluoren-2-yl)-7-t-butylpyreneYield 75.8%

Reagents, catalysts & solvents

2
HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

A mixed solution of 10.0 g of 1-bromo-7-t-butyl-3-(4-chlorophenyl)pyrene, 5.86 g of 9,9-dimethylfluoren-2-yl boronic acid, 0.016 g of bis(triphenylphosphine)palladium dichloride, 33 ml of an aqueous 1.5M sodium carbonate solution and 112 ml of 1,2-dimethoxyethane was heated and stirred for 3 hours under a nitrogen stream and under refluxing. After the mixture was cooled to room temperature, 223 ml of water was added, and this was extracted with 236 ml of toluene. The organic layer was washed with 640 ml of an aqueous sodium chloride solution two times, dried with magnesium sulfate, and evaporated, 50 ml of 2-propanol was added, and the mixture was stirred for 2 hours, and filtered. After the mixture was vacuum dried, 9.5 g of 1-(4-chlorophenyl)-3-(9,9-dimethylfluoren-2-yl)-7-t-butylpyrene was obtained.

Workup

  1. temperatureunder refluxing
  2. extractionthis was extracted with 236 ml of toluene
  3. washThe organic layer was washed with 640 ml of an aqueous sodium chloride solution two times
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. addition50 ml of 2-propanol was added
  7. stirringthe mixture was stirred for 2 hours
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-1afcc02df5f645b09852a0908612ffea
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916275B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes