Sodium Hydroxide → {2-[2-Chloro-4-(methylsulfonyl)phenoxy]phenoxy}acetic acid

HRID 1675634Notes

Reaction equation

HRID 1675634 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9].[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][C:22](F)=[C:21]([Cl:26])[CH:20]=1)(=[O:18])=[O:17].[OH-].[Na+]>CN(C=O)C>[Cl:26][C:21]1[CH:20]=[C:19]([S:16]([CH3:15])(=[O:18])=[O:17])[CH:24]=[CH:23][C:22]=1[O:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 22783(o-Hydroxyphenoxy)acetic acidHCID 24758Sodium hydrideHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzene

Product 1

HCID 58516141{2-[2-Chloro-4-(methylsulfonyl)phenoxy]phenoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydride (60% disp. oil, 0.24 g) was added to a solution of (2-hydroxyphenoxy) acetic acid (0.5 g) in DMF (20 ml) and stirred at 40° C. for 30 min. The product from example 7 step (ii) (0.62 g) was added, then the mixture heated at 75° C. for 30 h. 2M Sodium hydroxide solution was added and extracted with ethylacetate. The aqueous layer was acidified with 2M hydrochloric acid and extracted with ethyl acetate. The organics were dried, evaporated under reduced pressure and the residue purified by RPHPLC, yield 0.21 g.

Workup

  1. temperaturethe mixture heated at 75° C. for 30 h
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethyl acetate
  4. customThe organics were dried
  5. customevaporated under reduced pressure
  6. customthe residue purified by RPHPLC, yield 0.21 g

Sources & evidence

ORD record
ord-c13982af25aa4b788b6fcfea351c7669
Source dataset
uspto-grants-2011_08
Patent number
US08003703B2

Reaction notes

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