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

HRID 1811956Notes

Reaction equation

HRID 1811956 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 The solid
  5. washwas rinsed with DCM (3×50 ml)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-78d7e20109f1435eb70d3486a9ec0935
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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