Trifluoroacetic acid → HCID 45140203, compound

HRID 870032Notes

Reaction equation

HRID 870032 reaction equation
[Br:1][C:2]1[S:3][C:4]([Cl:16])=[CH:5][C:6]=1[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[Br:1][C:2]1[S:3][C:4]([Cl:16])=[CH:5][C:6]=1[CH2:7][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 451402022-Bromo-5-chloro-α-(3-chlorophenyl)-3-thiophenemethanol

Product 1

HCID 45140203HCID 45140203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-5-chloro-3-thienyl)(3-chlorophenyl)methanol from Example 1, Step 4 (2.50 g, 7.40 mmol) in dichloromethane at r.t. was added trifluoroacetic acid (5.70 mL, 74.0 mmol) (a red solution formed) followed by triethylsilane (5.91 mL, 37.0 mmol) (red solution turned into yellow) and the mixture was stirred at r.t. for 30 min. and concentrated. The residue was co-evaporated with toluene and then pumped under high vacuum. The crude was purified by flash chromatography (100% hexanes) to give the desired product as a colorless oil.

Workup

  1. customformed)
  2. concentrationconcentrated
  3. customThe crude was purified by flash chromatography (100% hexanes)

Sources & evidence

ORD record
ord-536102a4f29443f09320379067be3275
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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