Iodine → HCID 14744202, compound

HRID 724835Notes

Reaction equation

HRID 724835 reaction equation
[Mg].II.Cl[CH2:5][C:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7].[S:15](Cl)([Cl:18])(=[O:17])=[O:16].P([O-])([O-])([O-])=O>C1COCC1>[CH3:7][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:14])[CH2:5][S:15]([Cl:18])(=[O:17])=[O:16]

Participants

7

Reactant 5

HCID 807IodineHCID 1061PhosphateHCID 24648Sulfuryl chlorideHCID 68191Neophyl chlorideHCID 5462224Magnesium

Product 1

HCID 14744202HCID 14744202, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In a flask under argon were placed magnesium turnings (0.8 g, 0.036 mol), dry THF (10 mL) and a iodine crystal. Then, 1-chloro-2-methyl-2-phenylpropane (5 mL, 0.031 mol) in THF (15 mL) was added slowly and the reaction mixture was refluxed for 30 min. It was then allowed to cool to room temperature and finally it was cooled to -70° C. and sulfuryl chloride (2.5 mL, 0.031 mol) in THF (10 mL) was added dropwise. The reaction was allowed to warm up to room temperature and was stirred at this temperature overnight. The resulting solution was poured into diluted phosphate buffer and extracted with EtOAc (3×). Evaporation of the solvent afforded the title compound (4.6 g, 65%).

Workup

  1. customIn a flask under argon were placed
  2. temperaturethe reaction mixture was refluxed for 30 min
  3. temperaturefinally it was cooled to -70° C.
  4. temperatureto warm up to room temperature
  5. extractionextracted with EtOAc (3×)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cfbef0cd94774b0785b14ce79abdd45e
Source dataset
uspto-grants-1998_01
Patent number
US05705504

Reaction notes

Loading…