4-Bromothiophenol → HCID 67434549, compound

HRID 1810682Notes

Reaction equation

HRID 1810682 reaction equation
[CH3:1][C:2]([CH3:5])([O-])C.[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.[Br:15]C1CC1>CS(C)=O.CCOCC>[Br:15][C:12]1[CH:13]=[CH:8][C:9]([CH:5]2[CH2:2][CH2:1]2)=[CH:10][C:11]=1[SH:14]

Participants

6

Reactant 3

HCID 660494-BromothiophenolHCID 78037BromocyclopropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67434549HCID 67434549, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a degassed solution of potassium tert-butoxide (2.08 g, 18.51 mmol) in dry dimethylsulphoxide (6 mL), 4-bromo-benzenethiol (3.5 g, 18.5 mmol) was added and the mixture was stirred for 15 min at ambient temperature under nitrogen. Bromocyclopropane (4.4 mL, 55.5 mmol) was added afterwards and the reaction mixture was heated at 80° C. for 24 h in a sealed vessel. The mixture was cooled, diluted with ether (150 mL) and washed with water (100 mL). The aqueous layer was extracted with ether (3×50 mL). Combined organic extracts were finally dried with anhydrous magnesium sulfate. 1-Bromo-4-cyclopropyl-sulfanyl-benzene was obtained after evaporation of the solvent as yellow liquid.

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 24 h in a sealed vessel
  2. temperatureThe mixture was cooled
  3. washwashed with water (100 mL)
  4. extractionThe aqueous layer was extracted with ether (3×50 mL)
  5. dry with materialCombined organic extracts were finally dried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-65f3fb4031dd4fc9b74e108300b49a89
Source dataset
uspto-grants-2013_01
Patent number
US08362016B2

Reaction notes

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