Benzoyl Peroxide → HCID 55298631, compound

HRID 426243Notes

Reaction equation

HRID 426243 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:10][CH2:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 19867370Pyridine, 2-fluoro-4,6-dimethyl- (9CI)

Product 1

HCID 55298631HCID 55298631, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Fluoro-4,6-dimethyl-pyridine (4.25 g, 34 mmol) was refluxed with N-chlorosuccinimide (4.99 g, 37.4 mmol) and benzoyl peroxide (822 mg, 3.4 mmol) in carbon tetrachloride (70 ml). After 3.5 hr., the mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:30)) to afford 740 mg (13%) of 4-chloromethyl-2-fluoro-6-methyl-pyridine as a yellow oil. 1H NMR (200 MHz, CDCl3) δ 2.51 (3H, s), 4.51 (2H, s), 6.77 (1H, s), 7.05 (1H, s).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:30))

Sources & evidence

ORD record
ord-3b0e6d11dd89466a9b788deb3ede8fc1
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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