Iodine → HCID 14141874, compound

HRID 501913Notes

Reaction equation

HRID 501913 reaction equation
[CH2:1]([Sn:5](CCCC)([C:12]1C=C[CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[I:22]I>CO>[CH2:1]([Sn:5]([I:22])([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 807IodineHCID 80932Stannane, dibutyldiphenyl-

Product 1

HCID 14141874HCID 14141874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

In a three-necked flask protected from light, dibutyl diphenyltin (10 g, 25.9 mmol) was solubilized in 50 mL of dry methanol. A solution of iodine (6.04 g, 23.76 mmol) in methanol was then added slowly. After stirring at room temperature for 16 hours, methanol was eliminated under vacuum. The residue was dissolved in petroleum ether and washed with a saturated aqueous solution of sodium thiosulphate. Organic layers were washed with a saturated sodium chloride solution and dried over MgSO4. Solvent was evaporated and the crude product was distilled using a Kugelrohr apparatus (rotating glass oven for fractionating distillation of small sample volumes at 60° C. A colourless oil was obtained (10.5 g, 24.0 mmol).

Workup

  1. washwashed with a saturated aqueous solution of sodium thiosulphate
  2. washOrganic layers were washed with a saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. customSolvent was evaporated
  5. distillationthe crude product was distilled
  6. distillationdistillation of small sample volumes at 60° C
  7. customA colourless oil was obtained (10.5 g, 24.0 mmol)

Sources & evidence

ORD record
ord-25e3eba801a54826b1fa09ba4e9ac10a
Source dataset
uspto-grants-2010_08
Patent number
US07772417B2

Reaction notes

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