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

HRID 1914413Notes

Reaction equation

HRID 1914413 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

Next, 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 gas stream and then 3.3 g of benzyltrimethylammonium tribromide dissolved in 10 ml of dichloromethane was added dropwise. This mixed solution was stirred at room temperature for 2 hours and 50 ml of water was poured into the solution, followed by extraction with 50 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. To the resulting solid, 10 ml of methanol was added, followed by stirring for 10 minutes and further filtration. Furthermore, 30 ml of hexane was added and, after stirring for 30 minutes, the solution was filtered and the filtrate was vacuum-dried to obtain 2.3 g of 1-bromo-7-t-butylpyrene.

Workup

  1. additionwas added dropwise
  2. extractionfollowed by extraction with 50 ml of dichloromethane
  3. washThe organic layer was washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. additionTo the resulting solid, 10 ml of methanol was added
  7. stirringby stirring for 10 minutes
  8. filtrationfurther filtration
  9. additionFurthermore, 30 ml of hexane was added
  10. stirringafter stirring for 30 minutes
  11. filtrationthe solution was filtered
  12. customthe filtrate was vacuum-dried

Sources & evidence

ORD record
ord-2fade89a391b49f79a9b60fbd51ed5c8
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

Loading…