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

HRID 577088Notes

Reaction equation

HRID 577088 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O.C1(C(OOC(=O)C2C=CC=CC=2)=O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][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 99%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution 2,4-dichloro-3-methylpyridine (2.0 g, 12.3 mmol) in anhydrous carbon tetrachloride (50 mL) was added recrystallized 1-bromopyrrolidine-2,5-dione (2.25 g, 12.6 mmol) and benzoyl benzenecarboperoxoate (400 mg, 1.6 mmol). The mixture was stirred at reflux for 2 hours. After cooling to room temperature, the solid material was removed by filtration and washed with carbon tetrachloride (2×10 mL). The filtrate was recovered and evaporated. The solid product was dried in vacuo, affording 3-(bromomethyl)-2,4-dichloropyridine (2.9 g, 99% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solid material was removed by filtration
  3. washwashed with carbon tetrachloride (2×10 mL)
  4. customThe filtrate was recovered
  5. customevaporated
  6. customThe solid product was dried in vacuo

Sources & evidence

ORD record
ord-275566c78c744176be85b611a931f739
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…