Iodine → 1-Cyano-4-[[(3-iodo-2-propynyl)oxy]methoxy]benzene

HRID 1856597Notes

Reaction equation

HRID 1856597 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][O:11][CH2:12][C:13]#[CH:14])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].[I:17]I>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:10][O:11][CH2:12][C:13]#[C:14][I:17])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 22131913HCID 22131913, compound

Product 1

HCID 221319071-Cyano-4-[[(3-iodo-2-propynyl)oxy]methoxy]benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 -Cyano-4-[(2-propynyloxy)methoxy]benzene (Intermediate II-i) (9.4 g, 0.05 mol) prepared in the above example 4 and 48% w/v aqueous sodium hydroxide solution (11.3 g) were added to methanol (75 g). Iodine (14.0 g, 0.055 mol) was then added to the solution in several portions while maintaining the inner temperature below 10° C. The reaction mixture was stirred for further 3 hours and the solvent was then evaporated off. The residue was extracted with toluene (10 ml) and the toluene layer was washed with distilled water. Toluene was then evaporated off to obtain a crude reaction product (15.3 g). The crude reaction product (15.3 g) was recrystallized from hexane (50 ml) to obtain the desired 1-cyano-4-[[(3-iodo-2-propynyl)oxy]methoxy]benzene (Derivative III-i)(12.6 g, 94% yield).

Workup

  1. temperaturewhile maintaining the inner temperature below 10° C
  2. customthe solvent was then evaporated off
  3. extractionThe residue was extracted with toluene (10 ml)
  4. washthe toluene layer was washed with distilled water
  5. customToluene was then evaporated off
  6. customto obtain a crude
  7. customwas recrystallized from hexane (50 ml)

Sources & evidence

ORD record
ord-0a3ddb90068d4a629a308a3bd19daf5e
Source dataset
uspto-grants-2000_11
Patent number
US06143311

Reaction notes

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