Chlorotrimethylsilane → 1-Bromo-3-(trimethylsiloxy)benzene

HRID 1464538Notes

Reaction equation

HRID 1464538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[Si:17]([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:8][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 115633-Bromophenol

Product 1

HCID 6158011-Bromo-3-(trimethylsiloxy)benzeneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A dry 5 1, 3-neck flask with mechanical stirrer, connected to a mineral oil bubbler, was charged with m-bromophenol (A) (150 g, 870 mmol), dry tetrahydrofuran (THF, 2 l) and triethylamine (132.1 g, 1.3 mol). The contents of the flask were cooled to 0° C., and chlorotrimethylsilane was added dropwise. A voluminous white precipitate was formed. The reaction was allowed to equilibrate to room temperature over a period of 21 h. The mixture was then filtered to remove triethylamine hydrochloride. Removal of solvents precipitated some remaining hydrochloride salt. The mixture was further purified by repeatedly adding hexane followed by filtration to yield 3-bromo-O-trimethylsilylphenol (B) (207 g, 97% yield).

Workup

  1. customA dry 5 1, 3-neck flask with mechanical stirrer
  2. customA voluminous white precipitate was formed
  3. filtrationThe mixture was then filtered
  4. customto remove triethylamine hydrochloride
  5. customRemoval of solvents
  6. customprecipitated some remaining hydrochloride salt
  7. customThe mixture was further purified by repeatedly adding hexane
  8. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-a973822d9f264fd28705d96c05de423a
Source dataset
uspto-grants-1994_04
Patent number
US05306604

Reaction notes

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