Methanol → 1-Bromo-7-(tert-butyl)pyrene

HRID 1404882Notes

Reaction equation

HRID 1404882 reaction equation
[C:1]([C:5]1[CH:18]=[C:17]2[C:19]3=[C:20]4[C:10]([CH:11]=[CH:12][CH:13]=[C:14]4[CH:15]=[CH:16]2)=[CH:9][CH:8]=[C:7]3[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.[Br-:23].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.O>ClCCl>[Br:23][C:13]1[C:14]2[C:20]3=[C:19]4[C:17](=[CH:16][CH:15]=2)[CH:18]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[C:7]4[CH:8]=[CH:9][C:10]3=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 118177682-Tert-butylpyreneHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 497657301-Bromo-7-(tert-butyl)pyreneYield 142.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Then, a mixed solution of 3 g (content 65%) of 2-t-butylpyrene, 50 ml of dichloromethane and 15 ml of methanol was cooled to 0° C. under a nitrogen stream, and 3.3 g of benzyltrimethylammonium tribromide dissolved in 10 ml of dichloromethane was added dropwise. After this mixed solution was stirred at room temperature for 2 hours, 50 ml of water was added, and this was extracted with 50 ml of dichloromethane. The organic layer was washed with 50 ml of water two times, dried with magnesium sulfate, and evaporated. To the resulting solid was added 10 ml of methanol, and the mixture was stirred for 10 minutes, and filtered. Further, 30 ml of hexane was added, and the mixture was stirred for 30 minutes, and filtered. After the resultant was vacuum dried, 2.3 g of 1-bromo-7-t-butylpyrene was obtained.

Workup

  1. additionwas added dropwise
  2. extractionthis was extracted with 50 ml of dichloromethane
  3. washThe organic layer was washed with 50 ml of water two times
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. additionTo the resulting solid was added 10 ml of methanol
  7. stirringthe mixture was stirred for 10 minutes
  8. filtrationfiltered
  9. additionFurther, 30 ml of hexane was added
  10. stirringthe mixture was stirred for 30 minutes
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-e21ea0c3b14341de82793ac4674136f7
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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