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

HRID 1428716노트

반응식

HRID 1428716 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.[CH2:15]([O:17][C:18](=[O:22])[CH:19](Cl)[CH3:20])[CH3:16].FC(F)(F)C(O)=O.Cl>CN(C)C=O.[Mn]>[F:14][C:4]1[CH:3]=[C:2]([CH:19]([CH3:20])[C:18]([O:17][CH2:15][CH3:16])=[O:22])[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 10807Ethyl 2-chloropropionateHCID 70847718N-(4-bromo-2-fluorobenzyl)methanesulfonamide

생성물 1

HCID 70855559Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate수율 39.3%

시약·촉매·용매 2

HCID 23930Manganese촉매HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

N-(4-bromo-2-fluorobenzyl)methanesulfonamide (29 g, 102.8 mmol) and ethyl-2-chloropropionate (18.26 g, 133.6 mmol) were dissolved in dimethylformamide (155 mL) in a protective gas atmosphere at room temperature. Subsequently, manganese (11.29 g, 205.6 mmol), (2,2′-bipyridine)nickel(II) dibromide (2.69 g, 7.2 mmol) and trifluoroacetic acid (1.48 mL) were added and the mixture was stirred at 65° C. for 36 h. The reaction mixture was cooled to room temperature, hydrolysed using 1 N HCl (50 mL) and extracted with diethyl ether (4×100 mL). The combined organic layer were washed with water (40 mL) and brine solution (40 mL) and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by column chromatography (eluent: diethyl ether/n-hexane 9:1) to afford ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate (12.27 g, 39%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with diethyl ether (4×100 mL)
  3. washThe combined organic layer were washed with water (40 mL) and brine solution (40 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by column chromatography (eluent: diethyl ether/n-hexane 9:1)

출처 및 근거

ORD 기록
ord-de3d54fd924a4b7fbd8702fe252758fd
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

반응 노트

불러오는 중…