Citric Acid → 2-(3-Fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 889387노트

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HRID 889387 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:15])[C:11](Br)([CH3:13])[CH3:12])[CH3:8].[F:16][C:17]1[CH:18]=[C:19]([OH:26])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.CCOC(C)=O>[CH2:7]([O:9][C:10](=[O:15])[C:11]([O:26][C:19]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([F:16])[CH:18]=1)([CH3:13])[CH3:12])[CH3:8]

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 5209483-Fluoro-4-nitrophenol

생성물 1

HCID 671311902-(3-Fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl ester수율 23%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Potassium carbonate (3.96 g, 29 mmol) and 2-bromo-2-methylpropanoic acid ethyl ester (4.47 g, 23 mmol; CAS Reg. No. 600-00-0) were added to a solution of 3-fluoro-4-nitrophenol (3 g, 19 mmol; CAS Reg. No. 394-41-2) in DMSO (50 ml). The mixture was stirred for 18 h at 100° C. 10% aqueous citric acid and EtOAc were added and the layers were separated. The organic layer was washed with brine and dried over MgSO4. The solid was filtered off and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/heptane) to obtain the title compound (1.19 g, 4.4 mmol; 23%) as yellow oil.

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, EtOAc/heptane)

출처 및 근거

ORD 기록
ord-9761bf432c7849d0abd1fe14d8c67fd3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252826B2

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