Dichlorodimethylsilane → Chloro(4-ethoxyphenyl)dimethylsilane

HRID 247658

Reaction equation

HRID 247658 reaction equation
[Mg].[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH3:3].[Cl:12][Si:13](Cl)([CH3:15])[CH3:14]>O1CCCC1>[Cl:12][Si:13]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:2][CH3:3])=[CH:6][CH:7]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 685234-BromophenetoleHCID 5462224Magnesium

Product 1

HCID 14014482Chloro(4-ethoxyphenyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 3.5 g (0.14 mole) of magnesium powder in 100 ml of dry tetrahydrofuran was added dropwise 17.5 g (0.14 mole) of p-bromophenyl ethyl ether during a one hour period. The mixture was warmed for one hour and then cooled to room temperature. The reaction mixture was added dropwise to a solution of dichlorodimethylsilane in 100 ml of dry tetrahydrofuran which was cooled to -78° C. Upon completion of addition the reaction mixture was allowed to warm to room temperature. Stirring was continued overnight. After dilution with hexane, the reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure, leaving a liquid residue. Distillation of this residue yielded 18 g of chloro(4-ethoxyphenyl)dimethylsilane as a clear, colorless oil, b.p. 79°-81° C./0.09 mm of Hg.

Workup

  1. temperatureThe mixture was warmed for one hour
  2. temperaturewas cooled to -78° C
  3. additionUpon completion of addition the reaction mixture
  4. temperatureto warm to room temperature
  5. filtrationAfter dilution with hexane, the reaction mixture was filtered through celite
  6. customthe solvent was evaporated under reduced pressure
  7. customleaving a liquid residue
  8. distillationDistillation of this residue

Sources & evidence

ORD record
ord-3447a11bccb34c50a85ae6c2c3bc3cdb
Source dataset
uspto-grants-1987_11
Patent number
US04709068

Linked notes

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