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

HRID 1670056Notes

Reaction equation

HRID 1670056 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

A mixed solution of 3 g of 2-tert-butylpyrene (65% content), 50 ml of dichloromethane and 15 ml of methanol was then cooled to 0° C. under a nitrogen stream, and a solution of 3.3 g of benzyltrimethylammonium tribromide in 10 ml of dichloromethane was added dropwise to the mixed solution. After the mixed solution was stirred at room temperature for 2 hours, 50 ml of water was added thereto, and the mixture was extracted with 50 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate, and then evaporated. Ten ml of methanol was added to the resulting solid and stirred for 10 minutes, and then the solid was separated by filtration. Thereafter, 30 ml of hexane was further added to the solid and stirred for 30 minutes, and then the solid was separated by filtration. The solid was dried under vacuum to give 2.3 g of 1-bromo-7-tert-butylpyrene.

Workup

  1. extractionthe mixture was extracted with 50 ml of dichloromethane
  2. washThe organic layer was washed twice with 50 ml of water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionTen ml of methanol was added to the resulting solid
  6. stirringstirred for 10 minutes
  7. customthe solid was separated by filtration
  8. additionThereafter, 30 ml of hexane was further added to the solid
  9. stirringstirred for 30 minutes
  10. customthe solid was separated by filtration
  11. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-17b5055b80fe48459faf3db3a0410add
Source dataset
uspto-grants-2011_08
Patent number
US07989802B2

Reaction notes

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