Chlorotrimethylsilane → HCID 178505940, compound

HRID 472776Notes

Reaction equation

HRID 472776 reaction equation
[Zn:1].[Br:2]CCBr.C[Si](Cl)(C)C.[Cl:11][C:12]1[C:13]([F:20])=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br>O1CCCC1>[Br-:2].[Cl:11][C:12]1[C:13]([F:20])=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][Zn+:1]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 23994ZincHCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzene

Product 1

HCID 178505940HCID 178505940, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon stream, zinc powder (113.02 g, 1.73 mol) was suspended in tetrahydrofuran (350 ml), and 1,2-dibromoethane is (1.207 ml, 14.00 mmol) and trimethylsilyl chloride (8.88 ml, 70.00 mmol) were added at 60° C. The mixture was stirred with heating at 30 min. A solution of 3-chloro-2-fluorobenzyl bromide (406.73 g, 1.82 mol) in tetrahydrofuran (700 ml) was added dropwise at 60° C. The mixture was stirred with heating for 1 hr to give a solution of 3-chloro-2-fluorobenzylzinc bromide.

Workup

  1. additionwere added at 60° C
  2. temperaturewith heating at 30 min
  3. stirringThe mixture was stirred
  4. temperaturewith heating for 1 hr

Sources & evidence

ORD record
ord-18e42108637a4289b57189424e255db4
Source dataset
uspto-grants-2014_01
Patent number
US08633219B2

Reaction notes

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