Triethylsilane → 1-(4-Chlorobutyl)-4-fluorobenzene

HRID 355996Notes

Reaction equation

HRID 355996 reaction equation
C([SiH](CC)CC)C.[Cl:8][CH2:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=O>FC(F)(F)C(O)=O>[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 197503-(4-Fluorobenzoyl)propyl chloride

Product 1

HCID 30168891-(4-Chlorobutyl)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (22.5 ml; 0.141 mol) was added dropwise to a cold (~0° C.) stirring mixture of 4-chloro-4'-fluoro-butyrophenone (10 ml; 0.0613 mol) in trifluoroacetic acid (47 ml). The reaction mixture was stirred at room temperature under nitrogen for 6 hours. The reaction was quenched with brine and extracted with diethyl ether. The organic extract was dried (MgSO4) and evaporated under vacuum giving the desired compound as an oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature under nitrogen for 6 hours
  2. customThe reaction was quenched with brine
  3. extractionextracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-fd04131e36f04a06960a49b4dd1cc09f
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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