Benzoyl Peroxide → 2-(Bromomethyl)-6-chloro-pyridine

HRID 2041303Notes

Reaction equation

HRID 2041303 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C1C(=O)N([Br:16])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 876016-Chloro-2-picoline

Product 1

HCID 220327372-(Bromomethyl)-6-chloro-pyridineYield 41.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of 2-chloro-6-methylpyridine (5.46 g, 42.8 mmol), NBS (8.38 g, 47.08 mmol), and benzoyl peroxide (500 mg, 2.06 mmol) in carbon tetrachloride (80 mL) for 20 h at 85° C. Cool to ambient temperature, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/toluene (4:3) to provide the title compound as a white solid (3.64 g, 41%).

Workup

  1. temperatureHeat
  2. filtrationfilter
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/toluene (4:3)

Sources & evidence

ORD record
ord-74bfa6f990224920bbf8ea8a92b475de
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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