N-bromobutanimide → 2-Bromo-5-bromomethylpyridine

HRID 1054032Notes

Reaction equation

HRID 1054032 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1C(=O)N([Br:16])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:16])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Synthesized from 2-bromo-5-methylpyridine (3.00 g, 17.40 mmol), NBS (3.41 g, 19.20 mmol) and DBPO (230 mg, 0.80 mmol) in carbon tetrachloride according to Method A. Yield: 2.56 g (59%); lachrymatory yellow needles; 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.14 (s, 2H), 7.47 (d, J=8.2 Hz, 1H), 7.59 (d, J=8.2 Hz, 1H), 8.38 (s, 1H); MS (ESI): m/z=252.37 [M+H]+.

Sources & evidence

ORD record
ord-ee81b77b87cb42c1988cdda60ae1a7d9
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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