Chlorotrimethylsilane → HCID 178478089, compound

HRID 491513

Reaction equation

HRID 491513 reaction equation
[Zn:1].BrCCBr.C[Si]([Cl:10])(C)C.[Cl:11][C:12]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Cl>O1CCCC1>[Cl-:10].[Cl:11][C:12]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][Zn+:1]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 23994ZincHCID 76790Dichlorobenzyl chloride

Product 1

HCID 178478089HCID 178478089, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Under an argon stream, to a suspension of zinc powder (55.1 g, 843 mmol) in tetrahydrofuran (THF; 56 ml) was added 1,2-dibromoethane (2.9 ml, 33.8 mmol), and the mixture was heated under reflux for 5 min. Subsequently, trimethylsilyl chloride (8.6 ml, 67.5 mmol) was added at 0° C., and the mixture was stirred at 0° C. for 5 min. A solution of 2,3-dichlorobenzyl chloride (82.4 g, 421.7 mmol) in THF (330 ml) was added dropwise under ice-cooling, and after the completion of the dropwise addition, the mixture was allowed to warm to room temperature. The mixture was stirred for 1 hr to give a solution of 2,3-dichlorobenzylzinc chloride in THF.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperaturecooling
  4. additionafter the completion of the dropwise addition
  5. temperatureto warm to room temperature
  6. stirringThe mixture was stirred for 1 hr

Sources & evidence

ORD record
ord-5a39f8bed747478d9d0d131a61047aa0
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Linked notes

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