Chlorotrimethylsilane → HCID 178505940, compound

HRID 875054Notes

Reaction equation

HRID 875054 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 8028TetrahydrofuranSolvent3×

Procedure

Under an argon stream, zinc powder (11 g, 267 mmol) was suspended in tetrahydrofuran (30 ml), 1,2-dibromoethane (0.15 ml, 1.8 mmol) and trimethylsilyl chloride (0.45 ml, 3.6 mmol) were added at 65° C., and the mixture was stirred with heating for 30 min. A solution of 3-chloro-2-fluorobenzyl bromide (41 g, 178 mmol) in tetrahydrofuran (100 ml) was added dropwise at 65° C., and the mixture was stirred with heating for 2 hr and allowed to cool to room temperature to give a solution of 1M 3-chloro-2-fluorobenzylzinc bromide in tetrahydrofuran. This was used in the next main step.

Workup

  1. temperaturewith heating for 30 min
  2. stirringthe mixture was stirred
  3. temperaturewith heating for 2 hr

Sources & evidence

ORD record
ord-fb78b935b62542bdb18300397b82967a
Source dataset
uspto-grants-2015_03
Patent number
US08981103B2

Reaction notes

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