Ethyl bromoacetate → Ethyl 2-[2,4-difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate

HRID 1771598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771598
[F:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[CH:12][C:11]=2[CH3:23])=[C:6]([F:24])[CH:5]=[CH:4][C:3]=1[OH:25].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CC(=O)CC>[F:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[CH:12][C:11]=2[CH3:23])=[C:6]([F:24])[CH:5]=[CH:4][C:3]=1[O:25][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 894454532,4-Difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methyl amino]phenol

Produkt 1

HCID 89444115Ethyl 2-[2,4-difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,4-difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methyl amino]phenol (124 mg, 0.361 mmol, 1.0 eq) and Cs2CO3 (176.5 mg, 0.542 mmol, 1.5 eq) in 2-Butanone (10 mL) was added ethyl bromoacetate (72.4 mg, 0.433 mmol, 1.2 eq) and the reaction stirred 30 min. The reaction was filtered and the filtrate evaporated in vacuo. The residue obtained was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as an oil/gum (100 mg, 65%).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue obtained
  4. customwas purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-ea9c8fcbb3154f0398de6212451c3766
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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