Sodium Iodide → HCID 22326847, compound

HRID 495487Notes

Reaction equation

HRID 495487 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([O:13][CH3:14])[C:4]=1[O-:5].[K+].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].Br[CH2:25][CH2:26][Cl:27]>CC#N>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([O:13][CH3:14])[C:4]=1[O:5][CH2:25][CH2:26][Cl:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 22326798HCID 22326798, compound

Product 1

HCID 22326847HCID 22326847, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of potassium 2,6-dimethoxy-4-nitrophenoxide (Step B, 3.3 g, 13.9 mmol), K2CO3 (5.8 g, 41.8 mmol), NaI (0.21 g, 1.39 mmol), and 1-bromo-2-chloroethane (11.6 mL, 139 mmol) in CH3CN (50 mL) was stirred and heated under reflux under N2 for 40 h when the color had turned pale brown. Filtration, washing the solids well with CH3CN and evaporating the filtrate gave 3,5-dimethoxy-4-(2-chloroethoxy)nitrobenzene as a pale brown solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under N2 for 40 h when the color
  3. filtrationFiltration
  4. washwashing the solids well with CH3CN
  5. customevaporating the filtrate

Sources & evidence

ORD record
ord-c9dc6c91cdd74a2cb084e2f0af03de02
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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