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

HRID 1161013Notes

Reaction equation

HRID 1161013 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 whilst 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 with a 1N solution of hydrochloric acid 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-09843f2c5f2d4822bad2fe323d22956e
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

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