4-Bromophenetole → 4-Ethoxyphenyldimethylsilane

HRID 893396Notes

Reaction equation

HRID 893396 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[CH:13]([SiH3:15])Cl.[CH3:16][Mg]Cl>O1CCCC1.O>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([SiH:15]([CH3:13])[CH3:16])=[CH:3][CH:4]=1)[CH3:10]

Participants

7

Reactant 4

HCID 685234-BromophenetoleHCID 5462224MagnesiumHCID 57353436(Dichloromethyl)silaneHCID 178418332HCID 178418332, compound

Product 1

HCID 713607484-EthoxyphenyldimethylsilaneYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A Grignard solution prepared from 481.4 g of 4-bromophenetole, 61.0 g of magnesium and 1820 ml of tetrahydrofuran is added dropwise at -40 ° C. to a solution of 316 g of dichloromethylsilane in 1450 ml cf anhydrous tetrahydrofuran. Stirring is subsequently continued for 1 hour at -40 ° C., and the mixture is allowed to slowly warm to room temperature. After 1175 ml of a 3M methylmagnesium chloride solution in tetrahydrofuran have been added, the mixture is refluxed for 1 hour and cooled to 30 ° C., and the excess Grignard reagent is decomposed by the dropwise addition of 1100 ml of water. The phases are separated, and the aqueous phase is extracted using 500 ml of tetrahydrofuran. The combined organic phases are freed from solvent in vacuo, and the crude product is distilled in a thin-layer evaporator. 417 g of crude product of a purity of 94.3% (GC) are obtained, which corresponds to a yield of 91.1% of theory. The boiling point at 0.012 bar is 78° to 82 ° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperaturecooled to 30 ° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted
  5. distillationthe crude product is distilled in a thin-layer evaporator

Sources & evidence

ORD record
ord-d527a845d7644a61b487110a85a940c2
Source dataset
uspto-grants-1992_06
Patent number
US05124470

Reaction notes

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