Pyrene → 1-Bromopyrene

HRID 1893138Notes

Reaction equation

HRID 1893138 reaction equation
[CH:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)Cl>[Br:24][C:8]1[C:7]2[C:16]3=[C:15]4[C:4](=[CH:5][CH:6]=2)[CH:3]=[CH:2][CH:1]=[C:14]4[CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 31423PyreneHCID 67184N-bromobutanimide

Product 1

HCID 1596271-BromopyreneYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

Pyrene (2 g, 9.9 mmol), NBS (1.78 g, 10 mmol) were dissolved in 20 mL of CHCl3 under dry nitrogen topped with a reflux condenser. The reaction was stirred at 65° C. and monitored by GC-MS until complete. After evaporation of the solvent the crude product was further purified by chromatography on silica gel using 20:1 petroleum ether 60-80: EtOAc as eluent to afford a yellow solid (2 gr, 72%). 1H-NMR (500 MHz, CD2Cl2): δ 8.02-8.11 (m, 4H), 8.17-8.24 (m, 4H), 8.41 (d, J=9.2 Hz, 1H). 13C-NMR (125 MHz, CD2Cl2): δ 120.2, 124.4, 125.4, 126.1, 126.2, 126.3, 127.1, 127.6, 128.2, 129.5, 130.0, 130.5, 131.1, 131.2, 131.4, 131.7. EI-MS: m/z M+ Calculated 280.0, found 280.0.

Workup

  1. customtopped with a reflux condenser
  2. customAfter evaporation of the solvent the crude product
  3. customwas further purified by chromatography on silica gel using 20:1 petroleum ether 60-80

Sources & evidence

ORD record
ord-b5109ff7b1a445c796469e55f25b4de7
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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