Water → Ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate

HRID 714856Notes

Reaction equation

HRID 714856 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].Br[CH2:19][CH2:20]Br.O>CN(C)C=O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([C:5]2([C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH2:20][CH2:19]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 67154748Ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl(4-nitrophenyl)acetate (5.0 g) in N,N-dimethylformamide (100 mL) was added sodium hydride (60% in mineral oil, 1.9 g) in an ice bath, and the mixture was stirred at room temperature for 20 min. To the reaction mixture was added 1,2-dibromoethane (4.1 mL) in an ice bath, and the mixture was stirred at the same temperature for 30 min, and the at room temperature for 1 hr. The reaction mixture was colled to 0° C., water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.0 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 min
  2. waitthe at room temperature for 1 hr
  3. customwas colled to 0° C.
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe obtained organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aa4d5ffe87534919a0c69d29352331fb
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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