N-bromobutanimide → 3-(Bromomethyl)pyridine-2-carbonitrile

HRID 1054037Notes

Reaction equation

HRID 1054037 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(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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 103754503-(Bromomethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Synthesized from 3-methylpicolinonitrile (1.00 g, 8.47 mmol), NBS (1.66 g, 9.31 mmol) and DBPO (103 mg, 0.42 mmol) in CCl4 according to Method A. Yield: 616 mg, 3.12 mmol, 37%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 4.63 (s, 2H), 7.54 (dd, J=7.9, 4.9 Hz, 1H), 7.92 (dd, J=7.9, 1.5 Hz, 1H), 8.64 (dd, J=4.9, 1.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=26.8, 115.2, 127.1, 133.2, 138.1, 138.3, 150.5; MS (ESI): m/z=199.79 [M+H]+.

Sources & evidence

ORD record
ord-59b4c7ad060347c78010cfc2e0acec8d
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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