Benzoyl Peroxide → 2-(Bromomethyl)-4,6-dimethylpyridine

HRID 354025Notes

Reaction equation

HRID 354025 reaction equation
[N:1]1[C:6]([CH3:7])=[CH:5][C:4]([CH3:8])=[CH:3][C:2]=1[CH3:9].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][CH2:9][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[C:6]([CH3:7])[N:1]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 79532,4,6-TrimethylpyridineHCID 67184N-bromobutanimide

Product 1

HCID 222804052-(Bromomethyl)-4,6-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,4,6-collidine (1 mmole) in carbon tetrachloride was treated with NBS (5 mmole) and dibenzoyl peroxide (0.25 mmole) at 80° C. for 12 h. The reaction mixture was cooled to 0° C. and the precipitate was filtered. The filtrate was concentrated under vacuum. Chromatography gave 2-bromomethyl-4,6-dimethylpyridine.

Workup

  1. filtrationthe precipitate was filtered
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-443034ad2b6b407e8f5082253e455d28
Source dataset
uspto-grants-2004_06
Patent number
US06756360B1

Reaction notes

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