Water → Ethyl 2-chloro-3-(2-nitrophenyl)-3-oxopropanoate

HRID 2282222Notes

Reaction equation

HRID 2282222 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:3])=[O:2].S(Cl)([Cl:21])(=O)=O.O.CCOC(C)=O>C(OCC)C>[Cl:21][CH:11]([C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 10561837Ethyl 2-nitro-beta-oxobenzenepropanoate

Product 1

HCID 86649598Ethyl 2-chloro-3-(2-nitrophenyl)-3-oxopropanoateYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 3-(2-nitrophenyl)-3-oxopropanoate (2.0 g, 8.4 mmol) in diethyl ether (50 mL), was added sulfuryl chloride (1.37 g, 10 mmol) at 0° C., and the mixture was stirred for 3 h at rt. To the reaction mixture were added water (200 mL) and EtOAc (100 mL), and the mixture was stirred for 30 min. The organic layer was washed with brine (10 mL) and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound (1.7 g, 75%) as colorless oil.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a7a59d42c174399ba42b10811930ef8
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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