Benzoyl Peroxide → 5-Bromo-2-(bromomethyl)pyridine

HRID 1262210Notes

Reaction equation

HRID 1262210 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=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:3]=[CH:4][C:5]([CH2:8][Br:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 234380625-Bromo-2-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-methyl-pyridine (3.00 g, 17.4 mmol) was dissolved in Carbon tetrachloride (40.0 mL) and N-Bromosuccinimide (3.41 g, 19.2 mmol) was added. Benzoyl peroxide (0.23 g, 0.95 mmol) was added and the mixture was heated at 80° C. overnight. The reaction was cooled to room temperature and filtered to remove the succinimide. The filtrate was concentrated under reduced pressure. Purification by silica gel chromatography using 10% EtOAc/hex as the eluting solvent to obtain 5-bromo-2-bromomethyl-pyridine as a lachrymatory lilac oil (1.34 g, 31%). LCMS (m/e) 251 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.63 (d, 1H, J=2.2 Hz), 7.81 (dd, 1H, J=2.2 and 8.3 Hz), 7.34 (d, 1H, J=8.3 Hz), 4.50 (s, 2H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customto remove the succinimide
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-b99c6f506b814660b9ad19fd647c8507
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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