Triethylsilane → 1-Bromo-3-propylbenzene

HRID 2105022Notes

Reaction equation

HRID 2105022 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 882721-Propanone, 1-(3-bromophenyl)-

Product 1

HCID 138219241-Bromo-3-propylbenzeneYield 18.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1-(3-bromophenyl)propan-1-one (2.00 g, 9.39 mmol) in 10 mL TFA, was added triethylsilane (4.50 mL, 28.2 mmol). The mixture was stirred at rt for 20 h, then concentrated. The crude material was purified by flash chromatography to afford 350 mg of Intermediate 214.1 as a colorless oil.

Workup

  1. concentrationconcentrated
  2. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-0356ca20fc9c48c7ad68c0402590a617
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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