Iodine → p-methoxyphenyldimethylchlorosilane

HRID 1709016Notes

Reaction equation

HRID 1709016 reaction equation
[Mg].[CH3:2][Si:3]([CH3:6])(Cl)[Cl:4].II.Cl[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1>O1CCCC1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([Si:3]([CH3:6])([CH3:2])[Cl:4])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6398DichlorodimethylsilaneHCID 121674-ChloroanisoleHCID 5462224Magnesium2×

Product 1

HCID 10921557p-methoxyphenyldimethylchlorosilaneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The following were placed in a dry four-neck flask equipped with a stirrer, reflux condenser, addition funnel, and thermometer under a nitrogen blanket: 23.3 g (1.0 mol) powdered magnesium, 129.1 g (1.0 mol) dimethyldichlorosilane, and 200 mL tetrahydrofuran. A small quantity of iodine was added in order to activate the magnesium. Then, while cooling the flask to below 10 degrees Centigrade, a mixture of 142.6 g (1.0 mol) p-chloroanisole and 300 mL tetrahydrofuran was dripped in from the addition funnel with stirring over 5 hours. The reaction mixture was aged by heating under reflux for 2 hours, the precipitate was removed by suction filtration, and the filtrate was distilled to give 122 g (0.61 mol) product. The yield was 61%. The properties of this product are reported below.

Workup

  1. customThe following were placed in a dry four-neck flask
  2. customequipped with a stirrer
  3. temperaturereflux
  4. additioncondenser, addition funnel
  5. temperatureThen, while cooling the flask to below 10 degrees Centigrade
  6. temperatureby heating
  7. temperatureunder reflux for 2 hours
  8. customthe precipitate was removed by suction filtration
  9. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-cbcf095c7baa484fa0dc643856a881a0
Source dataset
uspto-grants-1990_08
Patent number
US04946921

Reaction notes

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