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

HRID 2105031Notes

Reaction equation

HRID 2105031 reaction equation
[Br: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>[Br: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 705081-(3-Bromo-4-fluorophenyl)ethan-1-one

Product 1

HCID 187118742-Bromo-4-ethyl-1-fluorobenzeneYield 68.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3′-bromo-4′-fluoroacetophenone (6.80 g, 31.3 mmol) in 31 mL TFA, was added triethylsilane (15 mL). The mixture was stirred at rt for 20 h, then concentrated. The crude product was purified by flash chromatography (100% hexanes, 2×) to afford 4.33 g of Intermediate 228.1 as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-6c8064900fea4c94b9bce494d35a99e2
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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