Water → 2-[4-(4-Bromo-2-fluorophenoxy)phenoxy]propionic acid methyl ester

HRID 4457

Reaktionsgleichung

Reaktionsgleichung von HRID 4457
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([F:16])[CH:3]=1.Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:22][O:21][C:19](=[O:20])[CH:18]([O:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([Br:1])=[CH:3][C:4]=2[F:16])=[CH:12][CH:11]=1)[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 135337314-(4-Bromo-2-fluorophenoxy)phenol

Produkt 1

HCID 135337252-[4-(4-Bromo-2-fluorophenoxy)phenoxy]propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (5.66 g, 0.02 mol) from Step V, methyl 2-bromoproprionate (3.34 g, 0.02 mol) and potassium carbonate (3.06 g, 0.22 mol) in DMSO (30 ml) was stirred, under an atmosphere of nitrogen, at room temperature for 18 hours. The mixture was poured into water (300 ml), and the resulting mixture extracted with ether (2×100 ml). The ether extracts were combined, washed with water (100 ml), dried (MgSO4), and the solvent evaporated to give the desired 2-[4-(4-bromo-2-fluorophenoxy)phenoxy]propionic acid; methyl ester as a yellow oil (6.0 g, 81%); RI=1.5628; NMR (CDCl3) was consistent with the assigned structure. The carbon and hydrogen content was as follows:

Aufarbeitung

  1. extractionthe resulting mixture extracted with ether (2×100 ml)
  2. washwashed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1f1e5d760a08437fbcdac96714805542
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725683

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