Ethyl 2-chloropropionate → Ethyl 2-(3-fluoro-4-nitrophenyl)propanoate

HRID 238921Notes

Reaction equation

HRID 238921 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH2:17]([O:19][C:20](=[O:24])[CH:21](Cl)[CH3:22])[CH3:18]>CN(C=O)C>[F:7][C:8]1[CH:13]=[C:12]([CH:21]([CH3:22])[C:20]([O:19][CH2:17][CH3:18])=[O:24])[CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 10807Ethyl 2-chloropropionateHCID 738951-Fluoro-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 12879863Ethyl 2-(3-fluoro-4-nitrophenyl)propanoateYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of potassium t-butoxide (20 mmol) in DMF (20 mL) was added a mixture of 2-fluoro-nitrobenzene (10 mmol) and ethyl-2-chloropropionate (10 mmol) at 0° C. dropwise. After being stirred for 10 min at 0° C., the mixture was quenched by 1 N HCl solution, diluted with water and extracted with diethyl ether several times. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:10) as eluant to afford ethyl 2-(3-fluoro-4-nitrophenyl)propionate (1-1, SU-654).

Workup

  1. customthe mixture was quenched by 1 N HCl solution
  2. additiondiluted with water
  3. extractionextracted with diethyl ether several times
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-0fbf866d9f15456097d65ecc3742a89a
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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