Water → Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

HRID 1471676노트

반응식

HRID 1471676 반응식
[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][CH:5](C(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].O.[Cl-].[Li+]>CS(C)=O>[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

5

반응물 3

HCID 962Water2회HCID 433294Lithium ChlorideHCID 67983387Diethyl 2-(2-bromo-6-chlorobenzyl)malonate

생성물 1

HCID 67982372Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Diethyl 2-(2-bromo-6-chlorobenzyl)malonate (13.0 g, 35.7 mmol), water (1.29 mL, 71.5 mmol) and lithium chloride (3.03 g, 71.50 mmol) in dimethylsulfoxide (75 mL) were heated to +185° C. for 1 h. The solution was allowed to cool. 75 mL of water was added. The mixture was extracted with ethyl acetate. The organic phase was washed with water and aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered and the solvent was removed by rotary evaporation to give the title compound. Yield: 7.34 g, 70%. 1H NMR (500 MHz, CDCl3) δ ppm 1.27-1.30 (m, 3H) 2.55-2.61 (m, 2H) 3.27-3.33 (m, 2H) 4.16-4.21 (m, 2H) 7.02 (t, 1H) 7.31-7.35 (m, 1H) 7.45-7.50 (m, 1H). MS m/z 293.0 [M+H]+.

후처리

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-bf30eeae73224437a1780998dc140f49
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012457B2

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