Thiophenol → HCID 14348393, compound

HRID 1650732Notes

Reaction equation

HRID 1650732 reaction equation
BrBr.Cl[CH2:4][CH2:5][CH2:6][C:7](=[O:9])[CH3:8].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+]>C(Cl)Cl.CO>[C:10]1([S:16][C:6]2([C:7]([CH3:8])=[O:9])[CH2:4][CH2:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 24408BromineHCID 799932-Pentanone, 5-chloro-

Product 1

HCID 14348393HCID 14348393, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 134 g (0.83 mol) of bromine in 130 ml of methylene chloride is added dropwise with stirring at 10° C. to a solution of 100 g (0.83 mol) of 5-chloropentan-2-one in 400 ml of methylene chloride. The reaction mixture is stirred for 1 hour at room temperature, then washed with water and dilute, aqueous sodium carbonate solution and dried over sodium sulphate. The mixture is concentrated by removing the solvent under reduced pressure, and the residue is taken up in 200 ml of methanol and 91.5 g (0.83 mol) of thiophenol are added at 5° C. with stirring. A mixture of 93 g of potassium hydroxide powder in 500 ml of methanol is then added dropwise. The reaction mixture is first stirred at room temperature for 2 hours and then at 40° C. for 4 hours. The mixture is subsequently concentrated by removing the solvent under reduced pressure and the residue which remains is taken up in methylene chloride. The organic solution is washed successively with water, dilute aqueous sodium carbonate solution and again with water, then concentrated under reduced pressure and then subjected to a vacuum distillation. In this manner, 76.8 g (48% of theory) of methyl 1-phenylmercaptocyclopropyl ketone of boiling point 155° C./20 mbar are obtained.

Workup

  1. washwashed with water
  2. additiondilute
  3. dry with materialaqueous sodium carbonate solution and dried over sodium sulphate
  4. concentrationThe mixture is concentrated
  5. customby removing the solvent under reduced pressure
  6. stirringwith stirring
  7. additionis then added dropwise
  8. stirringThe reaction mixture is first stirred at room temperature for 2 hours
  9. waitat 40° C. for 4 hours
  10. concentrationThe mixture is subsequently concentrated
  11. customby removing the solvent under reduced pressure
  12. washThe organic solution is washed successively with water, dilute aqueous sodium carbonate solution and again with water
  13. concentrationconcentrated under reduced pressure
  14. distillationsubjected to a vacuum distillation

Sources & evidence

ORD record
ord-9fc3afd51a97499083610c412f4a9ea4
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

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