2-Thiocresol → 1-(Cyclopropylsulfanyl)-2-methylbenzene

HRID 70563

Reaction equation

HRID 70563 reaction equation
[CH3:1][C:2]([CH3:5])([O-])C.[K+].BrC1CC1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18]>CS(C)=O.[Cl-].[Na+].O>[CH:5]1([S:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH3:11])[CH2:2][CH2:1]1

Participants

6

Reactant 3

HCID 87122-ThiocresolHCID 78037BromocyclopropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 579565761-(Cyclopropylsulfanyl)-2-methylbenzene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

Potassium t-butoxide (994 mg) and bromocyclopropane (2.92 g) were added to a solution of 2-methylbenzenethiol (1.05 g) in dimethyl sulfoxide (10 mL), and the mixture was stirred at 100° C. for 9.5 hours. The reaction solution was cooled to room temperature and brine was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1-(cyclopropylsulfanyl)-2-methylbenzene as an orange oil (1.41 g, quant.).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-53b183a844474fc5ab095796eb2aef6d
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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