Chlorotrimethylsilane → HCID 178504308, compound

HRID 1647008Notes

Reaction equation

HRID 1647008 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5]C=C(Br)C=1.[CH3:9][Si:10](Cl)([CH3:12])[CH3:11].[CH:14]([Mg:17]Cl)([CH3:16])[CH3:15].[Mg].[Br:20]CCBr>O1CCCC1>[CH3:9][Si:10]([CH3:12])([CH3:11])[O:7][C:6]1[CH:1]=[CH:16][C:14]([Mg:17][Br:20])=[CH:15][CH:5]=1

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 78084-BromophenolHCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 178418918HCID 178418918, compound

Product 1

HCID 178504308HCID 178504308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.8 g of p-bromophenol in 15 ml of tetrahydrofuran and then 5.75 ml of trimethylsilyl chloride were added to 50 ml of a solution of 0.9M of isopropyl magnesium chloride per liter of tetrahydrofuran and the resulting solution was poured over 1.2 g of magnesium turnings. A little 1,2-dibromoethane and then 2 ml of hexamethylphosphortriamide were added to the mixture which was refluxed for 21/2 hours to obtain a solution of 4-trimethylsilyloxy-phenyl magnesium bromide.

Workup

  1. temperaturewas refluxed for 21/2 hours

Sources & evidence

ORD record
ord-cbd1b89c5c294459b7b563645505d7d0
Source dataset
uspto-grants-1993_01
Patent number
US05182381

Reaction notes

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