Triethylsilane → 1-Bromo-3-propylbenzene

HRID 1872004Notes

Reaction equation

HRID 1872004 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>FC(F)(F)C(O)=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-propylbenzene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3'-bromopropiophenone (25 g) and triethylsilane (57 ml) in trifluoroacetic acid (50ml) was heated at reflux for 16 hours. The reaction mixture was evaporated under reduced pressure and the residue was purified by chromatography eluting with isohexane. Yield 25.14 g. The subtitle compound was contaminated with 17 mole % of 3-(1-propenyl)bromobenzene. Used directly in the next step. 1H NMR: δ(CDCl3) 7.32(m,2H), 7.10(m,2H), 2.55(t,2H), 1.61(m,2H), 0.90(t3H).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue was purified by chromatography
  4. washeluting with isohexane

Sources & evidence

ORD record
ord-4a56c3f007474818b4be2542a1478eba
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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