6-Methylchrysene → 6-Bromomethylchrysene

HRID 399644

Reaktionsgleichung

Reaktionsgleichung von HRID 399644
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1.[Br:20]N1C(=O)CCC1=O>ClC1C=CC=CC=1.CO.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][CH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1

Komponenten

6

Edukt 2

HCID 155646-MethylchryseneHCID 67184N-bromobutanimide

Produkt 1

HCID 109361336-BromomethylchryseneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7187Benzoyl PeroxideKatalysatorHCID 887MethanolLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 6-methylchrysene (4,85 g, 20 mmol), N-bromosuccinimide (3.60 g, 20.2 mmol), and benzoyl peroxide (0.242 g, 1.0 mmol) in chlorobenzene (100 mL) was heated under nitrogen at 80° C. After 1 hour, NMR analysis indicated that the starting material had been consumed. The solution was cooled to 50° C. at which point a solid precipitate had formed. The mixture was diluted with methanol (100 mL) and further cooled to ambient temperature. The mixture was filtered and the solid washed with methanol to give 4.87 g (76% yield) of 6-bromomethylchrysene. 1H NMR (CDCl3) 5.17 (s, 2H), 7.25 (m, 4 H), 8.0 (t, J=8.7 Hz, 2 H), 8.31 (m, 1 H), 8.67 (d, J=9.0 Hz), 8.75 (d, J=9.0 Hz, 1 H), 8.81 (m, 2 H).

Aufarbeitung

  1. customhad been consumed
  2. customhad formed
  3. temperaturefurther cooled to ambient temperature
  4. filtrationThe mixture was filtered
  5. washthe solid washed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-7dea783f879b4e408878849a522b38ad
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821387

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