Potassium Iodide → (4-Iodophenylethynyl)trimethylsilane

HRID 2262329Notes

Reaction equation

HRID 2262329 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:13]=[CH:12][C:10](N)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].N([O-])=O.[Na+].[I-:18].[K+]>Cl>[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:13]=[CH:12][C:10]([I:18])=[CH:9][CH:8]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 110524294-[(Trimethylsilyl)ethynyl]anilineHCID 23668193Sodium Nitrite

Product 1

HCID 11808725(4-Iodophenylethynyl)trimethylsilaneYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

As shown in the following Reaction 2, 250 mg (1.32 mmol) of 4-trimethylsilylethynylaniline obtained in A of Example 1-1 was melted in 3 mL of hydrochloric acid at the temperature of 0° C., and 94 mg (1.37 mmol, 1.04 eq) of sodium nitrite was added thereto, and then the reaction solution was stirred for 1 hour. After completion of stirring, 280 mg (1.69 mmol, 1.28 eq) of potassium iodide was added to the reaction solution, and then the reaction solution was stirred at room temperature for 12 hours. Next, the reaction solution was extracted with ether 2 times and 1 time with 1M sodium chloride aqueous solutions 1 time. The organic solvent layer was dehydrated with magnesium sulfate, filtered, and then distilled under reduced pressure. The compound distilled under reduced pressure was purified with an alumina column chromatography (mobile phase: hexane) to obtain 360 mg of 4-trimethylsilylethynyl iodobenzene with the yield of 92%. NMR data of the obtained compound is as follows. [1H NMR (400 MHz, CDCl3): δ 0.23-0.27 (m, 9H), 7.16 (d, 2H), 7.69 (d, 2H)].

Workup

  1. customobtained in A of Example 1-1
  2. additionwas added
  3. stirringAfter completion of stirring
  4. stirringthe reaction solution was stirred at room temperature for 12 hours
  5. extractionNext, the reaction solution was extracted with ether 2 times and 1 time with 1M sodium chloride aqueous solutions 1 time
  6. filtrationfiltered
  7. distillationdistilled under reduced pressure
  8. distillationThe compound distilled under reduced pressure
  9. customwas purified with an alumina column chromatography (mobile phase: hexane)

Sources & evidence

ORD record
ord-3b967c2ef80a4622b227c53c6895959b
Source dataset
uspto-grants-2010_12
Patent number
US07850872B2

Reaction notes

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