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

HRID 2235389

Reaction equation

HRID 2235389 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=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:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27628635-Fluoro-2-methylpyridine

Product 1

HCID 247293132-(Bromomethyl)-5-fluoropyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-fluoro-2-methyl-pyridine (0.75 g) (J. Med. Chem. 1989, 32, 1970) in CCl4 (25 ml) is added N-bromosuccinimide (0.96 g; 5.4 mmol) and benzoyl peroxide (200 mg; 0.8 mmol). The mixture is heated at reflux for 3 h, cooled to RT and stirred for additional 12 h. The suspension is filtered through celite and the filtrate is washed with Na2SO4, dried over MgSO4 and evaporated. The crude material (0.22 g) containing approximately 50% of the dibrominated species is used without further purification.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 h
  3. filtrationThe suspension is filtered through celite
  4. washthe filtrate is washed with Na2SO4
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additionThe crude material (0.22 g) containing approximately 50% of the dibrominated species
  8. customis used without further purification

Sources & evidence

ORD record
ord-38844669a7d5413e81148bcc4f606c06
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Linked notes

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