Chlorotrimethylsilane → HCID 178505940, compound

HRID 875059Notes

Reaction equation

HRID 875059 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 a nitrogen stream, zinc powder (18.8 kg, 287 mol) was suspended in tetrahydrofuran (130 L), 1,2-dibromoethane (470 g, 2.50 mol) was added at 60° C., and the mixture was stirred at the same temperature for 30 min. Trimethylsilyl chloride (560 g, 3.10 mol) was added to this suspension at room temperature, and the mixture was stirred with heating for 30 min. A solution of 3-chloro-2-fluorobenzyl bromide (54.0 kg, 242 mol) in tetrahydrofuran (65 L) was added dropwise at 0° C., and the mixture was stirred at 20° C. for 3 hr. The remaining zinc was filtered off to give a solution of 1M 3-chloro-2-fluorobenzylzinc bromide in tetrahydrofuran. This was used in the next main step.

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating for 30 min
  3. stirringthe mixture was stirred at 20° C. for 3 hr
  4. filtrationThe remaining zinc was filtered off

Sources & evidence

ORD record
ord-bcabe4b75d834c598f89b0ee30906d33
Source dataset
uspto-grants-2015_03
Patent number
US08981103B2

Reaction notes

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