HCID 55138441, compound → HCID 57656007, compound

HRID 2041447Notes

Reaction equation

HRID 2041447 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:5]=[CH:6][CH:7]=1>[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][S:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 55138441HCID 55138441, compound

Product 1

HCID 57656007HCID 57656007, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

Heat 2-(3-bromo-phenylthio)-1-phenyl-ethanone (4 g, 13 mmol) in polyphosphoric acid (4g) at 80° C. for 4 h. Add EtOAc and water to the mixture and wash with saturated aqueous NaHCO3 and brine. Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Slurry the residue in hexane and purify by chromatography on silica gel eluting with hexane to give the desired intermediate that is used without further purification (2.7 g, 72%). MS (GCMS) m/z: 289 M+.

Workup

  1. washAdd EtOAc and water to the mixture and wash with saturated aqueous NaHCO3 and brine
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. custompurify by chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-b46bda9f5715426ead1a3df56f4ed803
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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