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

HRID 910843Notes

Reaction equation

HRID 910843 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[C:6]([OH:14])[CH:5]=1.[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]>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:14][C:6]1[CH:5]=[C:4]([F:3])[CH:9]=[CH:8][C:7]=1[CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzeneHCID 673913704-Fluoro-2-hydroxyphenylacetic acid

Product 1

HCID 11660456{2-[2-Chloro-4-(methylsulfonyl)phenoxy]-4-fluorophenyl}acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% wt. disp. oil, 0.176 g) was added to a solution of the product from step (vi) (0.34 g) in dry DMF (10 ml) and stirred at RT for 1 h before adding the product from example 3 step (vii) (0.416 g). The mixture was heated at 80° C. for 1 h, then partitioned between 2M hydrochloric acid/ethyl acetate. The organics were dried, evaporated under reduced pressure and the residue purified by reverse phase HPLC. Yield 0.064 g

Workup

  1. temperatureThe mixture was heated at 80° C. for 1 h
  2. custompartitioned between 2M hydrochloric acid/ethyl acetate
  3. customThe organics were dried
  4. customevaporated under reduced pressure
  5. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f78782eac0c04a929fd4932a1e388541
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

Loading…