Benzoyl Peroxide → 3-(Bromomethyl)pyridine-2-carbonitrile

HRID 251249Notes

Reaction equation

HRID 251249 reaction equation
[CH3:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=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][CH2:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 103754503-(Bromomethyl)pyridine-2-carbonitrileYield 52.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-methylpicolinonitrile (1.0 g, 8.47 mmol) in CCl4 (43 ml) was added NBS (1.81 g, 10.16 mmol) and benzoyl peroxide (32 mg, 1.27 mmol) and the mixture stirred at relux for 16 hours. The reaction was concentrated in vacuo to afford a black oil. Purification via column chromatography on silica gel (EtOAc:hexane, 1:9, v/v) afforded 3-bromomethyl-pyridine-2-carbonitrile as a white solid (0.87 g, 48%). 1H NMR (CDCl3) δ 4.64 (s, 2H), 7.53 (dd, 1H, J=4.4, 4.0 Hz), 7.94 (dd, 1H, J=6.1, 1.8 Hz), 8.66 (dd, 1H, J=2.6, 1.8 Hz).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto afford a black oil
  3. customPurification via column chromatography on silica gel (EtOAc:hexane, 1:9, v/v)

Sources & evidence

ORD record
ord-df957b3cb2e9497bbece113c3b9c95fe
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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