Water → 3-bromoperylene

HRID 1805748Notes

Reaction equation

HRID 1805748 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.C1C(=O)N([Br:28])C(=O)C1.O>CN(C=O)C>[Br:28][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[CH:1]=[CH:2][CH:3]=[C:4]4[C:19]=3[C:8]([C:9]3[C:20]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3)=[CH:7][CH:6]=[CH:5]4

Participants

5

Reactant 3

HCID 962WaterHCID 9142PeryleneHCID 67184N-bromobutanimide

Product 1

HCID 118097033-bromoperyleneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Following the scheme shown in FIG. 18, perylene (252 mg, 1 mmol) was dissolved in DMF (45 ml), and a solution of NBS (178 mg) dissolved in DMF (10 ml) was added gradually. This was agitated at room temperature for 24 hours. H2O (200 ml) was added, and the product was precipitated and suction filtered. The product was recrystallized with hexane to obtain yellow-brown compound (1) (187 mg, mixture).

Workup

  1. additionwas added gradually
  2. customthe product was precipitated
  3. filtrationsuction filtered
  4. customThe product was recrystallized with hexane

Sources & evidence

ORD record
ord-400ad061558948afa531065f93e087cf
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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