6-Methylchrysene → 6-Bromomethylchrysene

HRID 399644

Reaction equation

HRID 399644 reaction equation
[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

Participants

6

Reactant 2

HCID 155646-MethylchryseneHCID 67184N-bromobutanimide

Product 1

HCID 109361336-BromomethylchryseneYield 76%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-7dea783f879b4e408878849a522b38ad
Source dataset
uspto-grants-1998_10
Patent number
US05821387

Linked notes

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