Chlorotrimethylsilane → HCID 178506382, compound
Reaction equation
[Zn:1].[Br:2]CCBr.Cl[Si](C)(C)C.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1>O1CCCC1>[Br-:2].[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][Zn+:1])=[CH:14][CH:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In a dried flask was zinc powder (0.769 g, 11.76 mmol) suspended in anhydrous tetrahydrofuran (20 mL) under nitrogen. The resulting suspension was warmed to 60° C., then 1,2-dibromoethane (0.042 mL, 0.49 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.050 mL, 0.39 mmol) was added and stirred at room temperature for 1 h. Then, 1-(bromomethyl)-4-(trifluoromethoxy)benzene (2.5 g, 9.80 mmol) in tetrahydrofuran (5 mL) was added over 2 min, then stirring continued at room temperature for 22 h. The stirring was switched off to let the solids settle. The supernatant was used in next transformation
Workup
- customIn a dried flask was
- temperatureIt was cooled to room temperature
- stirringstirred at room temperature for 1 h
- stirringstirring
- waitcontinued at room temperature for 22 h
Sources & evidence
- ORD record
- ord-9446825273da4aa8a80e4e121617fd9d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415378B2
Reaction notes
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