Sodium Iodide → 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

HRID 1787516Notes

Reaction equation

HRID 1787516 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Cl.Cl[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 12074NitrofunginHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineYield 52.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-4-nitro phenol 10 g (57.6 mmol, 1 eq), 2-(chloromethyl)pyridine hydrogen chloride 9.45 g (57.6 mmol, 1 equiv), cesium carbonate (41.3 g, 126.8 mmol, 2.2 equiv) and sodium iodide 8.64 g (57.6 mmol, 1 equiv) were suspended in 200 mL acetonitrile. The reaction mixture was stirred at 60° C. for 5 h. The resulted suspension was filtered and washed with 400 mL water, yielding 2-(2-chloro-4-nitro-phenoxymethyl)-pyridine (8 g, 52%) as a red solid.

Workup

  1. filtrationThe resulted suspension was filtered
  2. washwashed with 400 mL water

Sources & evidence

ORD record
ord-3233defb327c4b7d8b281f575d61b5d9
Source dataset
uspto-grants-2009_03
Patent number
US07511048B2

Reaction notes

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