Chlorotrimethylsilane → HCID 178478089, compound

HRID 347879

Reaction equation

HRID 347879 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. Then, trimethylsilyl chloride (8.6 ml, 67.5 mmol) was added at 0° C. and the mixture was stirred at 0° C. for 5 min, after which a solution of 2,3-dichlorobenzyl chloride (82.4 g, 421.7 mmol) in THF (330 ml) was added dropwise with ice-cooling. After completion of the dropwise addition, the mixture was warmed to room temperature and 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 completion of the dropwise addition
  5. temperaturethe mixture was warmed to room temperature
  6. stirringstirred for 1 hr

Sources & evidence

ORD record
ord-6c552893a17c45cd95cacf07d34e3298
Source dataset
uspto-grants-2007_02
Patent number
US07176220B2

Linked notes

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