N-bromobutanimide → 1-Bromo-7-(tert-butyl)pyrene

HRID 1404887Notes

Reaction equation

HRID 1404887 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].[Br:21]N1C(=O)CCC1=O>O1CCCC1>[Br:21][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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118177682-Tert-butylpyrene

Product 1

HCID 497657301-Bromo-7-(tert-butyl)pyreneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a mixed solution of 120 g (content 79.2%) of 2-t-butylpyrene, and 3000 ml of tetrahydrofuran was added 69.66 g of N-bromosuccinimide under a nitrogen stream. This mixed solution was stirred at 30° C. for about 3 hours, and concentrated, 500 ml of methanol was added, and the mixture was stirred for about 1 hour, and filtered. To the resulting solid was added 500 ml of hexane, and the mixture was heated and stirred for about 1 hour, and filtered. After the resultant was vacuum dried, 106.9 g of 1-bromo-7-t-butylpyrene was obtained.

Workup

  1. concentrationconcentrated
  2. addition500 ml of methanol was added
  3. stirringthe mixture was stirred for about 1 hour
  4. filtrationfiltered
  5. additionTo the resulting solid was added 500 ml of hexane
  6. temperaturethe mixture was heated
  7. stirringstirred for about 1 hour
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-daba8cb79ec94af9a151687ca18165e3
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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