Chlorotrimethylsilane → HCID 178505822, compound
Reaction equation
[Zn:1].[Br:2]CCBr.Cl[Si](C)(C)C.Br[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[CH:14]=1>C1COCC1>[Br-:2].[F:23][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=1)[CH2:12][Zn+:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In a dried flask was zinc powder (1.526 g, 23.34 mmol) suspended in anhydrous THF (12.5 mL) under nitrogen. The resulting suspension was warmed to 60° C., then 1,2-dibromoethane (0.084 mL, 0.97 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.099 mL, 0.78 mmol) was added and stirred at room temperature for 20 min. Then, 1-(bromomethyl)-3-fluoro-5-(trifluoromethyl)benzene (5 g, 19.45 mmol) dissolved in anhydrous THF (12.5 mL) was added over 7 min and stirring continued at room temperature for 1 h, then stirring was switched off to let the solids settle. The supernatant was used in the next transformation.
Workup
- customIn a dried flask was
- temperatureIt was cooled to room temperature
- stirringstirred at room temperature for 20 min
- additionwas added over 7 min
- stirringstirring
- waitcontinued at room temperature for 1 h
- stirringstirring
Sources & evidence
- ORD record
- ord-54fd1c048d784cb8b497cc0bab2e91c6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415378B2
Reaction notes
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