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

HRID 1914425Notes

Reaction equation

HRID 1914425 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-].[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>[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

7

Reactant 4

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

Product 1

HCID 497657301-Bromo-7-(tert-butyl)pyreneYield 161.5%

Reagents, catalysts & solvents 2

HCID 53442637BenzyltrimethylammoniumtribromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Next, a mixed solution of 45.0 g (content: 83%) of 2-t-butylpyrene, 660 ml of dichloromethane and 220 ml of methanol was cooled to 0° C. under an argon gas stream and then 56.4 g of benzyltrimethylammonium tribromide dissolved in 100 ml of dichloromethane was added dropwise. This mixed solution was stirred at room temperature for 2.5 hours and 5.64 g of benzyltrimethylammonium tribromide was added, followed by stirring for 1.5 hours. After the organic layer was isolated by pouring 250 ml of water into this mixed solution, the aqueous layer was extracted twice with 250 ml of dichloromethane. The combined organic layer was washed with 300 ml of water, dried over magnesium sulfate and then evaporated. To the resulting solid, 300 ml of methanol was added, followed by stirring and further filtration. To the resulting solid, 200 ml of hexane was added, and then the resulting solution was stirred, filtered and vacuum-dried to obtain 44.5 g of 1-bromo-7-t-butylpyrene.

Workup

  1. additionwas added dropwise
  2. stirringby stirring for 1.5 hours
  3. customAfter the organic layer was isolated
  4. extractionthe aqueous layer was extracted twice with 250 ml of dichloromethane
  5. washThe combined organic layer was washed with 300 ml of water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionTo the resulting solid, 300 ml of methanol was added
  9. stirringby stirring
  10. filtrationfurther filtration
  11. additionTo the resulting solid, 200 ml of hexane was added
  12. stirringthe resulting solution was stirred
  13. filtrationfiltered
  14. customvacuum-dried

Sources & evidence

ORD record
ord-a7eedf1a1cb341f5a2336a37956250c5
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

Loading…