Triethylsilane → 2-Chloro-4-ethyl-1-fluorobenzene

HRID 2105028

Reaction equation

HRID 2105028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 5204223'-Chloro-4'-fluoroacetophenone

Product 1

HCID 187118782-Chloro-4-ethyl-1-fluorobenzeneYield 28.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3′-chloro-4′-fluoroacetophenone (5.2 g, 30.1 mmol) in 30 mL TFA, was added triethylsilane (14.4 mL, 90.4 mmol). The mixture was stirred at rt for 15 h, then concentrated. The crude product was purified by flash chromatography (100% hexanes, 2×) to afford 1.35 g of Intermediate 221.1 as a colorless oil.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by flash chromatography (100% hexanes, 2×)

Sources & evidence

ORD record
ord-e628bb131f7d41c080af62910a34c143
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Linked notes

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