N-bromobutanimide → 1-Bromo-7-t-butyl-3-(4-chlorophenyl)pyrene

HRID 1404889Notes

Reaction equation

HRID 1404889 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:19]3=[C:20]4[C:10](=[CH:11][CH:12]=[C:13]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=5)[C:14]4=[CH:15][CH:16]=[C:17]3[CH:18]=1)[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[Br:28]N1C(=O)CCC1=O>O1CCCC1>[Br:28][C:11]1[C:10]2[C:20]3=[C:19]4[C:7](=[CH:8][CH:9]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:18]=[C:17]4[CH:16]=[CH:15][C:14]3=[C:13]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866607557-t-Butyl-1-(4-chlorophenyl)pyrene

Product 1

HCID 866607561-Bromo-7-t-butyl-3-(4-chlorophenyl)pyreneYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Then, to a mixed solution of 100.6 g of 7-t-butyl-1-(4-chlorophenyl)pyrene, and 1638 ml of tetrahydrofuran was added 53.5 g of N-bromosuccinimide under a nitrogen stream. This mixed solution was stirred at 30° C. for about 5 hours, and concentrated, 984 ml of methanol was added, and the mixture was stirred for about 1 hour, and filtered. To the resulting solid was added 539 ml of hexane, and the mixture was heated and stirred for about 1 hour, and filtered. After the resultant was vacuum dried, 112.0 g of 1-bromo-7-t-butyl-3-(4-chlorophenyl)pyrene was obtained.

Workup

  1. concentrationconcentrated
  2. addition984 ml of methanol was added
  3. stirringthe mixture was stirred for about 1 hour
  4. filtrationfiltered
  5. additionTo the resulting solid was added 539 ml of hexane
  6. temperaturethe mixture was heated
  7. stirringstirred for about 1 hour
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-9d971f30491243c4b343586e2946127c
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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