Chlorotrimethylsilane → HCID 15300442, compound

HRID 1581466Notes

Reaction equation

HRID 1581466 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[OH:16].CCCCCC.C([Li])CCC.[C:28]1([P:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)Cl)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:42][Si:43](Cl)([CH3:45])[CH3:44]>C(OCC)C>[CH3:42][Si:43]([O:16][C:3]1[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:7][C:2]=1[P:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:45])[CH3:44]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 66180ChlorodiphenylphosphineHCID 5198222-Bromo-4,6-di-tert-butylphenolHCID 178418339Butyllithium

Product 1

HCID 15300442HCID 15300442, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-30 °C

Procedure

Next, 5.0 g (17.5 millimole) of 2-bromo-4,6-di-tert-butylphenol described above was dissolved in 45 ml of dehydrated diethyl ether under nitrogen flow, and the solution was cooled down to −30° C. Then, 23.3 ml (37.3 millimole) of a hexane solution having an n-butyllithium concentration of 1.6 mole/liter was added thereto, and then the solution was stirred at a room temperature for 5 hours. The reaction mixture was cooled down to −30° C., and 3.26 ml (17.3 millimole) of diphenylchlorophosphine was added thereto and stirred at a room temperature for 8 hours. In this reaction solution, 2.6 ml (20.5 millimole) of trimethylsilyl chloride was added, and the solution was further stirred for 8 hours. Then, the solvent was distilled off under reduced pressure, and the residue was extracted with hexane. Subsequently, after the solvent was distilled off under reduced pressure, the residue was dissolved in hexane, and the solution was then cooled down to separate a precipitated solid matter, whereby 1.3 g (yield: 16%) of 4,6-di-tert-butyl-2-diphenylphosphinophenyl trimethylsilyl ether was obtained.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled down to −30° C.
  3. stirringstirred at a room temperature for 8 hours
  4. stirringthe solution was further stirred for 8 hours
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. extractionthe residue was extracted with hexane
  7. distillationSubsequently, after the solvent was distilled off under reduced pressure
  8. dissolutionthe residue was dissolved in hexane
  9. temperaturethe solution was then cooled down
  10. customto separate a precipitated solid matter

Sources & evidence

ORD record
ord-a63746a1a5194d39905ca9d4dada0254
Source dataset
uspto-grants-2004_05
Patent number
US06730626B2

Reaction notes

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