1,3-Dibromopropane → 1-[4-(3-Bromopropoxy)-3-methylmercaptophenyl]ethanone

HRID 1081016Notes

Reaction equation

HRID 1081016 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11][CH3:12].C([O-])([O-])=O.[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>C(#N)C>[Br:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11][CH3:12]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 30176621-(4-Hydroxy-3-(methylthio)phenyl)ethan-1-one

Product 1

HCID 100406381-[4-(3-Bromopropoxy)-3-methylmercaptophenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[4-hydroxy-3-(methylmercapto)phenyl]-ethanone (5.4 g; 30 mmol), K2CO3 (4.2 g), 1,3-dibromopropane (8 g, 39 mmol) in acetonitrile (150 ml) was heated at reflux for 3 hours and stirred at room temperature overnight. Acetonitrile was removed at reduced pressure and the residue was extracted into dichloromethane (250 ml). Insolubles were filtered off. The dichloromethane solution was concentrated. The crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l). The compound crystallized upon concentration, and the product (3.5 g, 39%) was recrystallized from ethanol (40 ml) to yield 1-[4-(3-bromopropoxy)-3-(methylmercapto)phenyl]ethanone as white needles, 2.0 g; m.p.=120°-122° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customAcetonitrile was removed at reduced pressure
  4. extractionthe residue was extracted into dichloromethane (250 ml)
  5. filtrationInsolubles were filtered off
  6. concentrationThe dichloromethane solution was concentrated
  7. customThe crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l)
  8. customThe compound crystallized upon concentration
  9. customthe product (3.5 g, 39%) was recrystallized from ethanol (40 ml)

Sources & evidence

ORD record
ord-fcb97bb7d8034acbaaa2dd7e98ed5cfe
Source dataset
uspto-grants-1996_12
Patent number
US05583145

Reaction notes

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