Hydrochloric Acid → Ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate

HRID 1400129Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:19](Br)[CH3:20].Cl>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:20][CH2:19]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 55 °C

Procedure

20 g of ethyl 4-nitrophenylacetate are dissolved in 30 ml of DMF and added dropwise to a suspension of 4 g of sodium hydride in 20 ml of DMF with ice-cooling. 8.5 ml of dibromoethane are subsequently added, and the mixture is stirred at 55° C. for 1 h. A further 5 g of sodium hydride and 8.5 ml of dibromoethane are added with ice-cooling, and the mixture is then stirred at 50° C. for 2 h. After cooling, the reaction mixture is stirred into a mixture of 100 ml of 1 N hydrochloric acid and 200 g of ice. The mixture is washed four times with 100 ml of diethyl ether each time, the combined organic phases once with 100 ml of sodium chloride solution, dried over sodium sulfate and, after filtration, evaporated to dryness in vacuo. The residue is purified by column chromatography (reversed phase). Yield: 8.5 g (38%) of ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate; LC-MS retention time: 2.01 min (“nonpolar” gradient);

Workup

temperaturecooling
temperaturecooling
stirringthe mixture is then stirred at 50° C. for 2 h
temperatureAfter cooling
washThe mixture is washed four times with 100 ml of diethyl ether each time
dry with materialthe combined organic phases once with 100 ml of sodium chloride solution, dried over sodium sulfate
filtrationafter filtration
customevaporated to dryness in vacuo
customThe residue is purified by column chromatography (reversed phase)

Sources & evidence

ORD record: ord-5d7ce069d1f5400eaa9120a6061f9230
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906930B2

Reaction notes

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