Hydrochloric Acid → Ethyl 2-(3-chloro-4-nitrophenyl)propanoate

HRID 1516756Notes

Reaction equation

HRID 1516756 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].Cl[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>C(OCC)(=O)C.CN(C=O)C>[Cl:7][C:8]1[CH:13]=[C:12]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69451-Chloro-2-nitrobenzeneHCID 10807Ethyl 2-chloropropionateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13213767Ethyl 2-(3-chloro-4-nitrophenyl)propanoateYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butylate (11.22 g, 2 eq) is added to a solution of DMF (80 ml) cooled down to 0° C. A solution of 1-chloro-2-nitrobenzene (7.87 g, 1 eq) and ethyl 2-chloropropanoate (7 ml, 1.1 eq) is added dropwise over 45 minutes to the mixture keeping the reaction temperature below 5° C. At the end of the addition, stirring is maintained for 2 hours at 0° C. then the mixture is hydrolyzed at this temperature by a 1N hydrochloric acid solution and ethyl acetate is added. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (eluent: heptane/dichloromethane 8:2 to 6:4) produces the expected compound in the form of a yellow oil (8.28 g; 64% yield).

Workup

  1. customthe reaction temperature below 5° C
  2. additionAt the end of the addition
  3. temperatureis maintained for 2 hours at 0° C.
  4. additionis added
  5. extractionAfter decantation and extractions
  6. washthe combined organic phases are washed with salt water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash chromatography on silica gel (eluent: heptane/dichloromethane 8:2 to 6:4)

Sources & evidence

ORD record
ord-06ed9330c31e41d39a1393b14ccbcf10
Source dataset
uspto-grants-2012_07
Patent number
US08227485B2

Reaction notes

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