N-bromobutanimide → 5-(Bromomethyl)-2-chloro-3-fluoropyridine

HRID 2199258Notes

Reaction equation

HRID 2199258 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 135413652-Chloro-3-fluoro-5-methylpyridine

Product 1

HCID 592970785-(Bromomethyl)-2-chloro-3-fluoropyridineYield 51%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

In 80 ml of carbon tetrachloride, 4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methylpyridine was dissolved. To this solution, 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added, and the mixture was heated under reflux overnight. After completion of the reaction, the reaction liquid was returned to room temperature, and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1). Thus, 3.06 g of 5-(bromomethyl)-2-chloro-3-fluoropyridine was obtained (Percentage Yield: 51%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. customwas returned to room temperature
  6. concentrationconcentrated under reduced pressure
  7. customThen, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-785eaaad52f34c2daa525f2b553ba60f
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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