Hydrochloric Acid → 4-[1-(Cyclopentylcarbonyl)cyclopropyl]-chlorobenzene
Reaction equation
[Mg].II.Br[CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:20]#N)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.Cl.CC[O:25]CC>>[CH:5]1([C:20]([C:17]2([C:14]3[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=3)[CH2:19][CH2:18]2)=[O:25])[CH2:9][CH2:8][CH2:7][CH2:6]1Participants
Procedure
2.4 g (0.1 mol) of magnesium chips are suspended in 10 ml ether. After the addition of a spatula-tip of iodine, 14.9 g (0.1 mol) of bromocyclopentane are slowly added dropwise to 40 ml of ether, the reaction being started off initially by gentle heating. After the addition has ended the mixture is refluxed for 30 minutes. Then a solution of 14.0 g (0.08 mol) of 1-(4-chlorophenyl)-1-cyclopropanecarbonitrile in 75 ml ether is added and refluxed for a further 3 hours. The reaction solution is poured onto ice water, adjusted to pH 3 with hydrochloric acid and extracted with ether. The organic extracts are dried and concentrated by evaporation. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (19:1 and 15:1).
Workup
- additionAfter the addition
- temperatureis refluxed for 30 minutes
- temperaturerefluxed for a further 3 hours
- additionThe reaction solution is poured onto ice water
- extractionextracted with ether
- customThe organic extracts are dried
- concentrationconcentrated by evaporation
- customThe residue is chromatographed on silica gel
- washeluted with petroleum ether/ethyl acetate (19:1 and 15:1)
Sources & evidence
- ORD record
- ord-4df6f944143c4707bc8d85cc2e726701
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248770B1
Reaction notes
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