Chlorotrimethylsilane → HCID 178440982, compound

HRID 1963339Notes

Reaction equation

HRID 1963339 reaction equation
[Zn:1].[Br:2]CCBr.Cl[Si](C)(C)C.Br[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=1>O1CCCC1>[Br-:2].[C:23]([C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=1)[CH2:12][Zn+:1])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 23994ZincHCID 44475071-(Bromomethyl)-3,5-di-tert-butylbenzene

Product 1

HCID 178440982HCID 178440982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

In a dried flask was zinc powder (2.493 g, 38.13 mmol) suspended in anhydrous tetrahydrofuran (23 mL) under nitrogen. The resulting suspension was warmed to 60° C., then 1,2-dibromoethane (0.137 mL, 1.59 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.161 mL, 1.27 mmol) was added and stirred at room temperature for 45 min. Then, 1-(bromomethyl)-3,5-di-tert-butylbenzene (9 g, 31.77 mmol) dissolved in anhydrous tetrahydrofuran (23.00 mL) was added over 10 min. Stirring continued at room temperature for 16 h, then stirring was switched off to let the solids settle. The supernatant was used in the next transformation.

Workup

  1. customIn a dried flask was
  2. temperatureIt was cooled to room temperature
  3. stirringstirred at room temperature for 45 min
  4. additionwas added over 10 min
  5. stirringStirring
  6. waitcontinued at room temperature for 16 h
  7. stirringstirring

Sources & evidence

ORD record
ord-9ab5194e2b78416584fd2599ed0cbb60
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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