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

HRID 889387ノート

反応式

HRID 889387 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9761bf432c7849d0abd1fe14d8c67fd3
出典データセット
uspto-grants-2012_08
特許番号
US08252826B2

反応ノート

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