Benzoyl Peroxide → 5-(Bromomethyl)-2-fluoropyridine

HRID 520748Notes

Reaction equation

HRID 520748 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(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 220506385-(Bromomethyl)-2-fluoropyridineYield 35%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-fluoro-5-methylpyridine in an amount of 500 mg (4.50 mmol) was dissolved in 50 mL of carbon tetrachloride, following which 1.20 g (6.76 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added and refluxing under heating was carried out for 2.5 hours. Following reaction completion, the reaction mixture was returned to room temperature, the solvent was removed by distillation under reduced pressure, and purification was carried out by silica gel column chromatography (hexane/ethyl acetate=19:1), giving 300 mg of 5-bromomethyl-2-fluoropyridine (yield, 35%).

Workup

  1. additionwere added
  2. temperaturerefluxing
  3. temperatureunder heating
  4. customreaction completion
  5. customwas returned to room temperature
  6. customthe solvent was removed by distillation under reduced pressure, and purification

Sources & evidence

ORD record
ord-e4bdd5f19a644a419be0f62af44db299
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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