Water → 1-Bromo-4-cyclopropylthiobenzene

HRID 732836Notes

Reaction equation

HRID 732836 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:13])([O-])C.[K+].C1(Br)CC1.O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:13]2[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 660494-BromothiophenolHCID 78037BromocyclopropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 223501051-Bromo-4-cyclopropylthiobenzeneYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolve 4-bromo-benzenethiol (2.00 g, 10.6 mmol) in dry DMSO (50 mL) under a nitrogen atmosphere. Add potassium tert-butoxide (1.30 g, 11.7 mmol) and stir until dissolved. Add cyclopropyl bromide (2.6 mL, 31.8 mmol) and heat the reaction to 80° C. for 2 days. Cool to room temperature and pour the reaction into water (500 mL). Extract the aqueous layer with Et2O (2×200 mL) and wash the combined organic layers with water (100 mL). Dry over sodium sulfate and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting the material with hexanes to give 1.73 g of 1-bromo-4-cyclopropylsulfanyl-benzene (72%).

Workup

  1. dissolutionuntil dissolved
  2. customthe reaction to 80° C. for 2 days
  3. additionpour
  4. extractionExtract the aqueous layer with Et2O (2×200 mL)
  5. washwash the combined organic layers with water (100 mL)
  6. dry with materialDry over sodium sulfate
  7. concentrationconcentrate in vacuo
  8. washChromatograph the residue on a SiO2 column eluting the material with hexanes

Sources & evidence

ORD record
ord-6ad97bdb173d4d21a282acd380427ddc
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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