Chlorotrimethylsilane → HCID 178448259, compound

HRID 634973Notes

Reaction equation

HRID 634973 reaction equation
[Zn:1].C(Br)CBr.C[Si](Cl)(C)C.[I:11][CH2:12][C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14]>C1COCC1>[I-:11].[CH2:12]([Zn+:1])[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 23994Zinc2×HCID 15327177HCID 15327177, compound

Product 1

HCID 178448259HCID 178448259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round flask including nitrogen preparation, internal thermometer and septum cap, which was heated in a vacuum and rinsed with argon, zinc powder (1.57 g, 24.0 mmol) was covered with a layer of THF (6 ml) and presented, and 1,2-dibromomethane (0.2 ml) was slowly added dropwise from a single-use syringe with cannula. Upon addition, heating was effected by means of a hot-air blast until the solvent was slightly boiling. After the reaction mixture was cooled to room temperature, trimethylsilylchloride (0.2 ml) was slowly added dropwise. By means of a hot-air blast, the mixture was again heated until it was slightly boiling, and stirring was continued for 5 minutes. Subsequently, 1-(2-iodo-1,1-dimethylethyl)benzene (neophyl iodide, 1.56 g, 6.0 mmol) was added within 5 minutes. Upon completion of the addition, the mixture was heated to 50° C. for 3 hours. The zinc insertion was observed by means of a GC analysis via iodolysis and hydrolysis of an aliquot of the reaction mixture.

Workup

  1. customIn a round flask including
  2. customnitrogen preparation, internal thermometer and septum
  3. customcap
  4. temperaturewhich was heated in a vacuum
  5. additionUpon addition
  6. temperatureheating
  7. temperatureBy means of a hot-air blast, the mixture was again heated until it
  8. additionUpon completion of the addition
  9. temperaturethe mixture was heated to 50° C. for 3 hours

Sources & evidence

ORD record
ord-0e49c8604fd8463695f8d40b3570f5d2
Source dataset
uspto-grants-2001_02
Patent number
US06184404B2

Reaction notes

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