Methyl-3,4,5-trichloro-6-(2-furyl)pyridine-2-carboxylate → Methyl 3,4,5-trichloro-6-(5-chloro-2-furyl)pyridine-2-carboxylate

HRID 1837463Notes

Reaction equation

HRID 1837463 reaction equation
I(Cl)(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.I([Cl:16])(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[CH3:28][O:29][C:30]([C:32]1[C:37]([Cl:38])=[C:36]([Cl:39])[C:35]([Cl:40])=[C:34]([C:41]2[O:42][CH:43]=[CH:44][CH:45]=2)[N:33]=1)=[O:31]>C(O)(=O)C.C(OCC)C>[Cl:38][C:37]1[C:32]([C:30]([O:29][CH3:28])=[O:31])=[N:33][C:34]([C:41]2[O:42][C:43]([Cl:16])=[CH:44][CH:45]=2)=[C:35]([Cl:40])[C:36]=1[Cl:39]

Participants

5

Reactant 2

HCID 22677507Methyl-3,4,5-trichloro-6-(2-furyl)pyridine-2-carboxylateHCID 57347110Benyltrimethylammonium tetrachloroiodate

Product 1

HCID 22677320Methyl 3,4,5-trichloro-6-(5-chloro-2-furyl)pyridine-2-carboxylateYield 51.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Benyltrimethylammonium tetrachloroiodate (292 mg, 0.70 mmol) was added to a solution of methyl-3,4,5-trichloro-6-(2-furyl)pyridine-2-carboxylate (101 mg, 0.33 mmol) in acetic acid (5 mL). After one hour, the suspension was diluted with diethyl ether and the organic mixture was washed with 0.1 N sodium thiosulphate, 0.1 N sodium bicarbonate and dried (MgSO4). The residue was purified by column chromatography (diethyl ether:hexane, 5:95) to give methyl 3,4,5-trichloro-6-(5-chloro-2-furyl)pyridine-2-carboxylate (58 mg, 0.17 mmol): 1H NMR (CDCl3): δ 7.41 (d, J=3.6 Hz, 1H), 6.40 (d, J=3.6 Hz, 1H), 4.05 (s, 3H).

Workup

  1. washthe organic mixture was washed with 0.1 N sodium thiosulphate, 0.1 N sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. customThe residue was purified by column chromatography (diethyl ether:hexane, 5:95)

Sources & evidence

ORD record
ord-00e056c2e271435c8505efa59029a4a7
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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