Chlorotrimethylsilane → HCID 178504749, compound

HRID 1963301Notes

Reaction equation

HRID 1963301 reaction equation
[Zn:1].[Br:2]CCBr.C[Si](Cl)(C)C.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1COCC1>[Br-:2].[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][Zn+:1])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 23994ZincHCID 27335814-(Methylsulfonyl)benzyl Bromide

Product 1

HCID 178504749HCID 178504749, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Zinc powder (2.81 g, 42.97 mmol) was suspended in THF (50 mL) under nitrogen and heated to 60° C. 1,2-dibromoethane (0.336 g, 1.79 mmol) was added and stirred for 15 min at 60° C. It was cooled to ambient temperature, TMSCl (0.156 g, 1.43 mmol) was added and stirred for 15 min at ambient temperature. 1-(Bromomethyl)-4-(methylsulfonyl)benzene (8.92 g, 35.81 mmol) dissolved in THF (50 mL) was added over 15 min and the resulting mixture was stirred at ambient temperature overnight. Stirring was stopped and the supernatant used in the next reaction.

Workup

  1. temperatureIt was cooled to ambient temperature
  2. stirringstirred for 15 min at ambient temperature
  3. additionwas added over 15 min
  4. stirringthe resulting mixture was stirred at ambient temperature overnight
  5. stirringStirring
  6. customthe supernatant used in the next reaction

Sources & evidence

ORD record
ord-6679f995d63f47899256164473dbf22e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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