N-bromobutanimide → 5-(Bromomethyl)-2-fluoropyridine

HRID 623286Notes

Reaction equation

HRID 623286 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 220506385-(Bromomethyl)-2-fluoropyridineYield 35.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

500 mg (4.50 mmol) of 2-fluoro-5-methyl pyridine was dissolved in 50 ml of carbon tetrachloride, 1.20 g (6.76 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 2.5 hours. After the reaction was completed, the reaction solution was returned to room temperature, and the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 300 mg (yield 35%) of 5-bromomethyl-2-fluoropyridine.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperaturerefluxed for 2.5 hours
  3. customwas returned to room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-9e9ddf3625034c6ab46db00d624ad403
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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