Benzoyl Peroxide → 3-(Bromomethyl)-2,4-dichloropyridine

HRID 577025Notes

Reaction equation

HRID 577025 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:17])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=1[Cl:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 212757642,4-Dichloro-3-methylpyridine

Product 1

HCID 589517013-(Bromomethyl)-2,4-dichloropyridineYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2,4-dichloro-3-methylpyridine (1.0 g, 6.17 mmol) in carbon tetrachloride (25 mL) was added NBS (1.09 g, 6.17 mmol) and a catalytic amount of benzoyl peroxide (0.15 g, 0.617 mmol). The reaction mixture was heated to reflux for 4 hours, and then cooled to room temperature and filtered. The filtrate was evaporated to afford 3-(bromomethyl)-2,4-dichloropyridine as a syrup (1.41 g, 95% yield), which was used in the next reaction without any further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5a97da5e3bfe4eda957e20f2a6a2d0f8
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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