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1,2-Dimethoxyethane → 7-t-Butyl-1-(4-chlorophenyl)pyrene

HRID 1404888
Notes
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Reaction equation

HRID 1404888 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=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.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>[C:18]([C:10]1[CH:9]=[C:8]2[C:17]3=[C:16]4[C:5](=[CH:4][CH:3]=[C:2]([C:26]5[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=5)[C:15]4=[CH:14][CH:13]=[C:12]3[CH:11]=1)[CH:6]=[CH:7]2)([CH3:21])([CH3:19])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 497657301-Bromo-7-(tert-butyl)pyrene

Product 1

HCID 866607557-t-Butyl-1-(4-chlorophenyl)pyreneYield 89.9%

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 962WaterSolvent

Procedure

Then, a mixed solution of 106.9 g of 1-bromo-7-t-butylpyrene, 54.5 g of 4-chlorophenylboronic acid, 0.223 g of bis(triphenylphosphine)dichloropalladium, 350 ml of an aqueous 2M sodium carbonate solution and 1586 ml of 1,2-dimethoxyethane was heated and stirred for about 5 hours under a nitrogen stream and under refluxing. After the mixture was cooled to room temperature, 640 ml of water was added, and this was extracted with 1170 ml of toluene. The organic layer was washed with 640 ml of water two times, dried with magnesium sulfate, and evaporated, 270 ml of toluene and 1350 ml of methanol were added, and the mixture was stirred for about 2 hours, and filtered. After the resultant was vacuum dried, 105.16 g of 7-t-butyl-1-(4-chlorophenyl)pyrene was obtained.

Workup

  1. temperatureunder refluxing
  2. extractionthis was extracted with 1170 ml of toluene
  3. washThe organic layer was washed with 640 ml of water two times
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. addition270 ml of toluene and 1350 ml of methanol were added
  7. stirringthe mixture was stirred for about 2 hours
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-fbdb218b766a48cfb18a6ea650c65100
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