Potassium Hydroxide → 1-(4-Fluoro-phenyl)-2-(3-methoxy-phenylsulfanyl)-ethanone

HRID 270386Notes

Reaction equation

HRID 270386 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[F:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=[O:20])[CH2:18]Br)=[CH:15][CH:14]=1>C(O)C.O.CCOC(C)=O>[F:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=[O:20])[CH2:18][S:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 849893-MethoxybenzenethiolHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 110331141-(4-Fluoro-phenyl)-2-(3-methoxy-phenylsulfanyl)-ethanoneYield 104.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

14.27 ml (115.0 mmol) 3-mercaptoanisole were added to a solution of 7.3 g (115.0 mmol) KOH in 120 ml ethanol and 50 ml water. 25.0 g (115.2 mmol) 4-fluorophenacyl bromide in 120 ml EtOAc were added slowly at 0° C. and the solution was stirred at RT over night. The suspension was concentrated and dissolved in EtOAc and water. The inorganic phase was extracted with EtOAc, the combined organic phases were washed with water and brine and dried over Na2SO4. Evaporation yielded 33.2 g crude 1-(4-Fluoro-phenyl)-2-(3-methoxy-phenylsulfanyl)-ethanone as light yellow liquid.

Workup

  1. concentrationThe suspension was concentrated
  2. dissolutiondissolved in EtOAc
  3. extractionThe inorganic phase was extracted with EtOAc
  4. washthe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation

Sources & evidence

ORD record
ord-90ef568bf7a14405b60c11a7e05dd754
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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