Dichlorodimethylsilane → Chloro[(4-methoxyphenyl)methyl]dimethylsilane

HRID 1252741Notes

Reaction equation

HRID 1252741 reaction equation
[Mg].[CH3:2][Si:3]([CH3:6])(Cl)[Cl:4].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1>C(OCC)C>[Cl:4][Si:3]([CH3:6])([CH3:2])[CH2:13][C:12]1[CH:15]=[CH:16][C:9]([O:8][CH3:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 699934-Methyloxybenzyl chlorideHCID 5462224Magnesium

Product 1

HCID 19781371Chloro[(4-methoxyphenyl)methyl]dimethylsilaneYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 2-liter three-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer were placed 31.0 g (1.28 mol) of magnesium powder, 129 g (1 mol) of dimethyldichlorosilane, and 500 ml of diethyl ether. With the flask cooled below 10° C., a mixture of 100 g (0.639 mol) of p-methoxybenzyl chloride and 250 ml of diethyl ether was added dropwise from the dropping funnel over 4 hours. After aging at room temperature for 1 hour, excess magnesium and magnesium chloride were removed by suction filtration. The filtrate was distilled to give 87.8 g (0.409 mol) of the desired product in a 64.0% yield.

Workup

  1. customIn a 2-liter three-neck flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureWith the flask cooled below 10° C.
  4. additionwas added dropwise from the dropping funnel over 4 hours
  5. customexcess magnesium and magnesium chloride were removed by suction filtration
  6. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-aa4d6f14677c4c478d6d88afc1129b60
Source dataset
uspto-grants-1988_05
Patent number
US04745169

Reaction notes

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