Benzoyl Peroxide → 2-Bromo-5-bromomethylpyridine

HRID 2103352Notes

Reaction equation

HRID 2103352 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Bromo-5-methylpyridine (5.00 g, 29.1 mmoles) and N-bromosuccinimide (5.22 g, 29.3 mmoles) were dissolved in carbon tetrachloride (40 mL) under nitrogen. Benzoyl peroxide (0.35 g, 1.4 mmoles) was added and the mixture heated at reflux for four hours. The mixture was cooled to room temperature, filtered, and washed with NaHCO3/H2O. The mixture was adsorbed onto silica gel and then chromatographed. eluting with a gradient of hexane to 10% ethyl acetate/hexane. Pure fractions were combined and concentrated to provide the desired mono-brominated product as a pale yellow solid, 3.60 g (49%). LC/MS (M+H)+ m/z=249.8, 251.8, 253.8.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for four hours
  3. filtrationfiltered
  4. washwashed with NaHCO3/H2O
  5. customchromatographed
  6. washeluting with a gradient of hexane to 10% ethyl acetate/hexane
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b2854da40d5e43c89bf41491e0fb97ee
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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