Hydrochloric Acid → Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate

HRID 1428723노트

반응식

HRID 1428723 반응식
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([F:14])[CH:3]=1.Cl[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>CN(C)C=O.FC(F)(F)C(O)=O.[Mn]>[F:14][C:4]1[CH:3]=[C:2]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 10807Ethyl 2-chloropropionateHCID 70847718N-(4-bromo-2-fluorobenzyl)methanesulfonamide

생성물 1

HCID 70855559Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate

시약·촉매·용매 3

HCID 6422Trifluoroacetic acid촉매HCID 23930Manganese촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of N-(4-bromo-2-fluorobenzyl)methanesulfonamide (2.94 g, 10.421 mmol) in dimethylformamide were added ethyl 2-chloropropionate (1.725 mL), manganese (1.145 g) and (2,2′-bipyridine)nickel(II)-dibromide (273 mg, mmol). 1-2 drops trifluoroacetic acid were added. The reaction mixture was stirred for 36 h at 60° C. After cooling down to room temperature, the mixture was hydrolysed by 1N HCl and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate (218 mg) was obtained.

후처리

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-afcb9a61fe6d4b4989e1f8b3adbbaf2d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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