Hydrochloric Acid → 4-Cyanophenyl cyclopropyl ketone
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14].Cl.O>CN(C=O)C.[Fe](Cl)(Cl)Cl>[C:13]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1)#[N:14]Participants
7
Conditions
- Temperature
- 70 °C
Procedure
22.5 g of 4-bromophenylcyclopropylmethanone (100 mmol) and 10.3 g of CuCN (100 mmol) are dissolved in 15 ml of DMF and heated under reflux, with stirring, for 4 hours. The suspension is allowed to cool down to 70° C. and is then poured into a solution consisting of 40 g of iron(III) chloride, 10 ml of conc. HCl and 60 ml of water. The mixture is stirred at 70° C. for 20 minutes. It is then extracted three times with 90 ml of toluene on each occasion. The combined organic phases are washed with 250 ml of 2N hydrochloric acid and with 250 ml of 2N sodium hydroxide solution, and then concentrated. The solid residue is triturated with petroleum ether and filtered off with suction.
Workup
- temperatureheated
- temperatureunder reflux
- additionis then poured into a solution
- stirringThe mixture is stirred at 70° C. for 20 minutes
- extractionIt is then extracted three times with 90 ml of toluene on each occasion
- washThe combined organic phases are washed with 250 ml of 2N hydrochloric acid and with 250 ml of 2N sodium hydroxide solution
- concentrationconcentrated
- customThe solid residue is triturated with petroleum ether
- filtrationfiltered off with suction
Sources & evidence
- ORD record
- ord-0aa1663d992d42c096efffb88880d13e
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06191282B1
Reaction notes
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