N-bromobutanimide → 2-(Bromomethyl)-6-chloro-pyridine

HRID 1769016Notes

Reaction equation

HRID 1769016 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClC(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][Br:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 876016-Chloro-2-picoline

Product 1

HCID 220327372-(Bromomethyl)-6-chloro-pyridineYield 77.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

6-Chloro-2-methylpyridine (20 g), (Ex Aldrich), N-bromosuccinimide (31 g), benzoyl peroxide (570 mg) and tetrachloromethane (250 ml) were heated together under reflux and under irradiation from a powerful lamp for 6 hours. After standard work-up and purification by column chromatography (silica; 5% ether in hexane), 6-chloro-2-bromomethylpyridine (25 g) was obtained.

Workup

  1. temperatureunder reflux and under irradiation from a powerful lamp for 6 hours
  2. customAfter standard work-up and purification by column chromatography (silica; 5% ether in hexane)

Sources & evidence

ORD record
ord-8437f73d637f4eeb861db404d9958066
Source dataset
uspto-grants-1995_01
Patent number
US05380732

Reaction notes

Loading…