Dichlorodimethylsilane → Chloro(4-ethoxyphenyl)dimethylsilane

HRID 726519Notes

Reaction equation

HRID 726519 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[Mg].[Cl:12][Si:13](Cl)([CH3:15])[CH3:14]>O1CCCC1>[Cl:12][Si:13]([CH3:15])([CH3:14])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 685234-BromophenetoleHCID 5462224Magnesium

Product 1

HCID 14014482Chloro(4-ethoxyphenyl)dimethylsilaneYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of p-bromophenetole (40.2 g, 0.2 mol) in tetrahydrofuran is added dropwise to a stirred mixture of magnesium turnings (4.86 g, 0.2 mol) in tetrahydrofuran under nitrogen. After the addition is complete, the reaction mixture is stirred at 60° C. for 45 minutes, cooled to room temperature and added dropwise to a solution of dichlorodimethylsilane (25.8 g, 0.2 mol) in tetrahydrofuran while maintaining the temperature below -60° C. The resultant reaction mixture is stirred at -65° C. for 15 minutes, stirred overnight at room temperature, diluted with hexanes, filtered through a pad of diatomaceous earth, concentrated in vacuo, diluted with additional hexanes and filtered through a second pad of diatomaceous earth. The resultant filtrate is concentrated in vacuo to obtain a brown liquid which is distilled to give the title product as a clear liquid (22.2 g, bp 81°-87° C./0.4 mm Hg).

Workup

  1. additionAfter the addition
  2. temperaturecooled to room temperature
  3. temperaturewhile maintaining the temperature below -60° C
  4. customThe resultant reaction mixture
  5. stirringis stirred at -65° C. for 15 minutes
  6. stirringstirred overnight at room temperature
  7. filtrationfiltered through a pad of diatomaceous earth
  8. concentrationconcentrated in vacuo
  9. additiondiluted with additional hexanes
  10. filtrationfiltered through a second pad of diatomaceous earth
  11. concentrationThe resultant filtrate is concentrated in vacuo
  12. customto obtain a brown liquid which
  13. distillationis distilled

Sources & evidence

ORD record
ord-61805803dedd421eb61bcb9a8e03fa30
Source dataset
uspto-grants-1998_01
Patent number
US05710102

Reaction notes

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