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

HRID 238921

반응식

HRID 238921 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0fbf866d9f15456097d65ecc3742a89a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642657B2

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