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

HRID 1383186Notes

Reaction equation

HRID 1383186 reaction equation
[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>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:12]=2)=[C:4]([F:16])[CH:3]=1

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (5.66 g, 0.02 mole) from Step V, methyl 2-bromoproprionate (3.34 g, 0.02 mole) and potassium carbonate (3.06 g, 0.22 mole) 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 (2×10 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%); R.I.=1.5628; NMR (CDCl3) was consistent with the assigned structure. The carbon and hydrogen content was as follows:

Workup

  1. extractionthe resulting mixture extracted with ether (2×10 ml)
  2. washwashed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-8f01bd8a59e846cc81e28c125efd11de
Source dataset
uspto-grants-1989_02
Patent number
US04808750

Reaction notes

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