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

HRID 222027

Reaction equation

HRID 222027 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-].[I-].[Na+].[C:16](#[N:18])[CH3:17]>>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:17][C:16]1[CH:4]=[CH:3][CH:2]=[CH:7][N:18]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 12074NitrofunginHCID 6410751Hydrogen chloride dimer

Product 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineYield 52%

Conditions

Temperature
60 °C

Procedure

2-chloro-4-nitro phenol 10 g (57.6 mmol, 1 eq), 2-pycolyl chloride hydrogen chloride 9.45 g (57.6 mmol, 1 equiv) cesium carbonate 41.3 (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-b1c8e9d82ccb4ffdab9f980fd3450f46
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Linked notes

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