1-Bromo-3-chloropropane → 1-[4-((3-Chloropropyl)thio]-3-methoxyphenyl]ethanone

HRID 744377Notes

Reaction equation

HRID 744377 reaction equation
[CH3:1][C:2]([C:4]1[CH:10]=[C:9]([O:11][CH3:12])[C:7](=[S:8])[CH2:6][CH:5]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23].C1CCCCC1>CC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][S:8][C:7]1[CH:6]=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[CH:10][C:9]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8078CyclohexaneHCID 11430Potassium CarbonateHCID 219601011-(4-Thio-3-methoxyphenyl)ethanone

Product 1

HCID 102442711-[4-((3-Chloropropyl)thio]-3-methoxyphenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 1-(4-thio-3-methoxyphenyl)ethanone (10.0 g, 54.9 mmol), potassium carbonate (9.0 g, 65.1 mmol), and acetone (100 ml) was stirred at reflux under nitrogen for 30 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (6.5 ml, 9.5 g, 60.4 mmol) dissolved in acetone (25 ml) was dripped into the reaction. After complete addition, the reaction was heated to reflux and stirred under nitrogen for 17 hours. After the reaction was carried to substantial completion, the reaction mixture was filtered and the resulting filter cake was washed with acetone. The filtrate was concentrated to provide an amber oil. A small sample was solidified by trituration with hot cyclohexane to provide 1-[4-[(3-chloropropyl)thio]-3-methoxyphenyl]ethanone as a yellow solid, 11.7 g, m.p.=53°-55° C.

Workup

  1. temperatureat reflux under nitrogen for 30 minutes
  2. customwas dripped into the reaction
  3. additionAfter complete addition
  4. temperaturethe reaction was heated
  5. temperatureto reflux
  6. stirringstirred under nitrogen for 17 hours
  7. filtrationthe reaction mixture was filtered
  8. filtrationthe resulting filter cake
  9. washwas washed with acetone
  10. concentrationThe filtrate was concentrated
  11. customto provide an amber oil

Sources & evidence

ORD record
ord-ea9e990638654df2a591ceddbb858170
Source dataset
uspto-grants-1996_09
Patent number
US05559117

Reaction notes

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