Hydrochloric Acid → 2-{4-[(5-Bromo-3-fluoropyridin-2-yl)oxy]phenoxy}propanoic acid

HRID 232253Notes

Reaction equation

HRID 232253 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.[Br:16][C:17]1[CH:18]=[C:19]([F:24])[C:20](F)=[N:21][CH:22]=1.Cl>CS(C)=O.O>[Br:16][C:17]1[CH:18]=[C:19]([F:24])[C:20]([O:3][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)=[N:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1011822-(4-Hydroxy-phenoxy)-propionic acidHCID 145496545-Bromo-2,3-difluoropyridine

Product 1

HCID 155928392-{4-[(5-Bromo-3-fluoropyridin-2-yl)oxy]phenoxy}propanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of NaOH (0.54 g, 0.013 mol) in a few ml of water was added to -2-(4-hydroxyphenoxy)propionic acid (1.22 g, 0.0067 mol) in 20 ml DMSO and the mixture was stirred for 20 minutes under N2. 5-Bromo-2,3-difluoropyridine (1.3 g, 0.0067 mol) was added and the mixture was stirred for 51/2 hours at 80°-90° C. The reaction mixture was poured into water, acidified with concentrated HCl to pH 1 and extracted into CH2Cl2. The solution was dried over Na2SO4 and the solvent was removed by rotary evaporation to yield a gum which became an off-white solid (0.78 g, 33%, M.P.94°-97° C.) upon standing.

Workup

  1. stirringthe mixture was stirred for 51/2 hours at 80°-90° C
  2. extractionextracted into CH2Cl2
  3. dry with materialThe solution was dried over Na2SO4
  4. customthe solvent was removed by rotary evaporation
  5. customto yield a gum which

Sources & evidence

ORD record
ord-0f788b3cd49949c6a9bd3ea6b0f15706
Source dataset
uspto-grants-1989_07
Patent number
US04851539

Reaction notes

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