Perylene → HCID 86650101, compound

HRID 1967658Notes

Reaction equation

HRID 1967658 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[Br:21]N1C(=O)CCC1=O>ClCCl>[Br-:21].[CH:16]1[C:17]2=[C:20]3[C:9]([C:8]4[C:19]5[C:4](=[CH:3][CH:2]=[CH:1][C:18]2=5)[CH:5]=[CH:6][CH:7]=4)=[CH:10][CH:11]=[CH:12][C:13]3=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 9142PeryleneHCID 67184N-bromobutanimide

Product 1

HCID 86650101HCID 86650101, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 3.0 g (11 mmol) of perylene was dissolved in 700 mL of dichloromethane, the solution was stirred for 5 minutes. To the solution, 2.11 g (12 mmol, 1.1 eq) of N-bromosuccinimide was dropwise added slowly at room temperature, followed by stirring overnight. The reaction solution was purified by silica gel column chromatography using a developing solvent adjusted to dichloromethane:hexane=1:1 to remove N-bromosuccinimide. After the solvent was concentrated, yellow crystals (yield 90%) were obtained. The compound was identified by 1H-NMR and ESI-MS.

Workup

  1. stirringby stirring overnight
  2. customThe reaction solution was purified by silica gel column chromatography
  3. customhexane=1:1 to remove N-bromosuccinimide
  4. concentrationAfter the solvent was concentrated

Sources & evidence

ORD record
ord-177f1645482f4df0b19fd57528cd26f2
Source dataset
uspto-grants-2013_04
Patent number
US08420865B2

Reaction notes

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