Trifluoroacetic acid → 1-(5-(4-Bromophenyl)thien-2-yl)-3-(2,3-dichloro-4-hydroxyphenyl)propan-1-one

HRID 416053Notes

Reaction equation

HRID 416053 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](=[O:25])[CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([Cl:23])[C:17]=3[Cl:24])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13](=[O:25])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([Cl:23])[C:17]=3[Cl:24])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 666242391-(5-(4-Bromophenyl)thien-2-yl)-3-(2,3-dichloro-4-hydroxyphenyl)prop-2-en-1-one

Product 1

HCID 591803301-(5-(4-Bromophenyl)thien-2-yl)-3-(2,3-dichloro-4-hydroxyphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(5-(4-Bromophenyl)thien-2-yl)-3-(2,3-dichloro-4-hydroxyphenyl)prop-2-en-1-one is dissolved in dichloromethane (0.7 g, 1.5 mol/L). Triethylsilane (2.1 eq.) and trifluoroacetic acid (8 eq.) are successively added dropwise. After stirring for 16 hours at room temperature, the reaction mixture is washed with water and then the dichloromethane is removed by evaporation under reduced pressure. The evaporation residue is purified by silica-gel chromatography

Workup

  1. washthe reaction mixture is washed with water
  2. customthe dichloromethane is removed by evaporation under reduced pressure
  3. customThe evaporation residue is purified by silica-gel chromatography

Sources & evidence

ORD record
ord-888da972a0e14a29867949a43521a5bb
Source dataset
uspto-grants-2012_01
Patent number
US08088819B2

Reaction notes

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