Bromine → 4-Bromo-1-(cyclopropylsulfanyl)-2-methylbenzene

HRID 70564Notes

Reaction equation

HRID 70564 reaction equation
[Br:1]Br.[CH:3]1([S:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.[Cl-].[Na+].O>[Br:1][C:10]1[CH:11]=[CH:12][C:7]([S:6][CH:3]2[CH2:5][CH2:4]2)=[C:8]([CH3:13])[CH:9]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 579565761-(Cyclopropylsulfanyl)-2-methylbenzene

Product 1

HCID 584527214-Bromo-1-(cyclopropylsulfanyl)-2-methylbenzeneYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Bromine (0.42 mL) was added to a solution of 1-(cyclopropylsulfanyl)-2-methylbenzene (1.35 g) in acetic acid (10 mL) under ice-cooling, and the mixture was stirred at room temperature for 17 hours. The reaction solution was ice-cooled and a saturated sodium thiosulfate solution and brine were 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 only) and the solvent was evaporated under reduced pressure. The precipitated solid was filtered and washed with hexane, after which the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a pale yellow oil (1.59 g, 80%).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane only) and the solvent
  8. customwas evaporated under reduced pressure
  9. filtrationThe precipitated solid was filtered
  10. washwashed with hexane
  11. customafter which the filtrate was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane only)

Sources & evidence

ORD record
ord-fba7a3f56f734ca2bb67d1a4d7a12f5c
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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