N-bromobutanimide → HCID 86660757, compound

HRID 1404890Notes

Reaction equation

HRID 1404890 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:20]3[C:21]4=[C:22]5[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=[C:13]5[CH:12]=[CH:11][C:10]4=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Br:33]N1C(=O)CCC1=O>O1CCCC1>[Br:33][C:9]1[C:10]2[C:21]3=[C:22]4[C:13](=[CH:12][CH:11]=2)[CH:14]=[C:15]([C:23]([CH3:26])([CH3:24])[CH3:25])[CH:16]=[C:17]4[CH:18]=[CH:19][C:20]3=[C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:6][CH:5]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86660758HCID 86660758, compound

Product 1

HCID 86660757HCID 86660757, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Then, to a mixed solution of 8.65 g of 1-(4-biphenylyl)-7-t-butylpyrene, and 126 ml of tetrahydrofuran was added 4.1 g of N-bromosuccinimide under a nitrogen stream. This mixed solution was stirred at 30° C. for about 3 hours, and concentrated, 126 ml of methanol was added, and the mixture was stirred for about 1 hour, and filtered. To the resulting solid was added 30 ml of tetrahydrofuran, the mixture was heated and dissolved, 180 ml of methanol was added, and the mixture was stirred for about 1 hour, and filtered. After the resultant was purified by silica gel column chromatography, the solid obtained by evaporation was washed with 126 ml of methanol, and vacuum dried to obtain 8.8 g of 1-bromo-3-(4-biphenylyl)-7-t-butylpyrene.

Workup

  1. concentrationconcentrated
  2. addition126 ml of methanol was added
  3. stirringthe mixture was stirred for about 1 hour
  4. filtrationfiltered
  5. additionTo the resulting solid was added 30 ml of tetrahydrofuran
  6. temperaturethe mixture was heated
  7. dissolutiondissolved
  8. addition180 ml of methanol was added
  9. stirringthe mixture was stirred for about 1 hour
  10. filtrationfiltered
  11. customAfter the resultant was purified by silica gel column chromatography
  12. customthe solid obtained by evaporation
  13. washwas washed with 126 ml of methanol, and vacuum
  14. customdried

Sources & evidence

ORD record
ord-a21b9ca106ab4d85b3de5d0178c27a3a
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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