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

HRID 1621543Notes

Reaction equation

HRID 1621543 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 100%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-fluoro-5-methyl-pyridine (15.00 mL, 135 mmol), N-bromosuccinimide (24.03 g, 135 mmol) and benzoyl peroxide (1.635 g, 6.75 mmol) in carbon tetrachloride (100 mL) was heated at reflux for 2.5 h. The mixture was cooled and filtered through a medium-fritted funnel. The solid was rinsed with DCM (3×50 ml). The filtrate was concentrated to give 5-(bromomethyl)-2-fluoropyridine (25.7 g, 135 mmol, 100% yield) as an orange oil. m/z (ESI, +ve ion) 191.9 (M+H)+. The mixture was immediately carried into the next step of the synthesis without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through a medium-fritted funnel
  5. washThe solid was rinsed with DCM (3×50 ml)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-27eab5bd776044629e2f1be3bec339b0
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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