Sodium hydride → 2-Bromo-1-methyl-4-(propylsulfinyl)benzene

HRID 2390274Notes

Reaction equation

HRID 2390274 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[H-].[Na+].I[CH2:13][CH2:14][CH3:15].[O-:16]I(=O)(=O)=O.[Na+]>CN(C=O)C.O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:13][CH2:14][CH3:15])=[O:16])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 127220873-Bromo-4-methylbenzene-1-thiolHCID 23667635Sodium periodate

Product 1

HCID 565939782-Bromo-1-methyl-4-(propylsulfinyl)benzene

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromo-4-methyl-benzenethiol (1.27 g; 6.25 mmol) in anhydrous DMF (12.5 ml) was treated with sodium hydride (300 mg; 7.5 mmol). Then reaction mixture was stirred at RT for 15 minutes, then the treated with 1-iodopropane (0.73 ml; 7.5 mmol). The reaction was stirred for 24 hours, before being quenched by dropwise addition of water. EtOAc was added and the layers separated. The organic layer was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in MeOH (13 mL), cooled to 0° C. and treated with a 0.5 M solution of sodium (meta)periodate in water (12.5 ml; 6.24 mmol). After stirring for 24 hours at RT, EtOAc and water were added and the phases separated and the organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a yellow sticky solid.

Workup

  1. customThen reaction mixture
  2. stirringThe reaction was stirred for 24 hours
  3. custombefore being quenched by dropwise addition of water
  4. additionEtOAc was added
  5. customthe layers separated
  6. washThe organic layer was washed with brine
  7. customdried on MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in MeOH (13 mL)
  11. temperaturecooled to 0° C.
  12. stirringAfter stirring for 24 hours at RT
  13. customthe phases separated
  14. dry with materialthe organic phase was dried over MgSO4
  15. concentrationconcentrated under reduced pressure
  16. customThe resulting residue was purified by flash column chromatography (silica)
  17. washeluting with cyclohexane containing
  18. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-0734a51cbf6c4cb98150d43c16be1a76
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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