Hydrochloric Acid → HCID 58869175, compound

HRID 2355198Notes

Reaction equation

HRID 2355198 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[OH:11])=[O:3].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN1C(=O)CCC1.O>[OH:11][C:5]1[CH:6]=[C:7]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:4]=1[C:2](=[O:3])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 58869175HCID 58869175, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-fluoro-2-hydroxyacetophenone (3.083 g, 20 mmol) in NMP (50 mL) were added thiophenol (2.054 ml, 20 mmol) and K2CO3 (8.293 g, 60 mmol). The reaction was heated at 110° C. overnight. Upon cooling the mixture was poured into water, acidified by addition of HCl (diluted) and extracted with Et2O. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 1-(2-hydroxy-4-phenylsulfanyl-phenyl)-ethanone (4.980 g of oil) that was used for the next step without further purification.

Workup

  1. temperatureUpon cooling the mixture
  2. extractionextracted with Et2O
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5dac548830e44ec823f8d9e902106b8
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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