Dimethyl Sulfoxide → 1-(3-Chlorophenyl)cyclobutane-1-carbonitrile

HRID 865664Notes

Reaction equation

HRID 865664 reaction equation
CS(C)=O.O.[Cl:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.Br[CH2:17][CH2:18][CH2:19]Br>CCOCC.CC(O)C>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2([C:14]#[N:15])[CH2:19][CH2:18][CH2:17]2)[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 80011,3-DibromopropaneHCID 73722m-Chlorophenylacetonitrile

Product 1

HCID 219019791-(3-Chlorophenyl)cyclobutane-1-carbonitrileYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

According to the procedure of Butler and Pollatz (Butler, D. E. and J. C. Pollatz, J. Org. Chem. 36:1308 (1971), a reaction flask fitted with a mechanical stirrer, pressure equalizing addition funnel and thermometer was charged, under nitrogen, with 162 ml of DMSO; 17.62 g (0.44 mol) of 60% Nail/oil dispersion was added in portions over 5 minutes. A 20° C. water bath was applied while a solution of 24.5 g (0.162 mol) of (3-chlorophenyl)acetonitrile and 35.9 g (0.195 mol) of 1,3-dibromopropane in Et2O (100 ml) was added during 75 minutes with good stirring at such a rate that the reaction temperature was kept below 33° C. The mixture was stirred at 20° C. for 2 hours when it was cooled in an ice bath and treated cautiously with 8 ml of 2-propanol. The mixture was stirred at 10° C. for 15 minutes when it was treated cautiously with 120 ml of H20 at such a rate that the reaction temperature was kept below 15° C. After 15 minutes, the layers were separated and the aqueous layer was extracted with 4 portions of Et2O. The extracts were combined with the organic layer and this mixture was dried (MgSO4) and concentrated. A red oil was separated from the mineral oil and distilled to give 15.8 g (51%) of the titled product, b.p. 106°-110° C. (0.9 mm Hg).

Workup

  1. custom36:1308 (1971), a reaction flask fitted with a mechanical stirrer
  2. additionaddition funnel
  3. additionwas added during 75 minutes
  4. customwas kept below 33° C
  5. stirringThe mixture was stirred at 20° C. for 2 hours when it
  6. temperaturewas cooled in an ice bath
  7. stirringThe mixture was stirred at 10° C. for 15 minutes when it
  8. additionwas treated cautiously with 120 ml of H20 at such a rate that the reaction temperature
  9. customwas kept below 15° C
  10. customthe layers were separated
  11. extractionthe aqueous layer was extracted with 4 portions of Et2O
  12. dry with materialthis mixture was dried (MgSO4)
  13. concentrationconcentrated
  14. customA red oil was separated from the mineral oil
  15. distillationdistilled

Sources & evidence

ORD record
ord-631583b79462422ab42ba5d752ef089e
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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