HCID 19101398, compound → HCID 9957292, compound

HRID 1975262Notes

Reaction equation

HRID 1975262 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([O:25]C)=[O:24])[CH:5]=[C:6]([Br:21])[C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)(=[O:10])=[O:9]>[OH-].[Na+]>[Br:21][C:6]1[CH:5]=[C:4]([CH2:22][C:23]([OH:25])=[O:24])[CH:3]=[C:2]([Br:1])[C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:19])[CH3:20])[CH:12]=1)(=[O:9])=[O:10]

Participants

3

Reactant 1

HCID 19101398HCID 19101398, compound

Product 1

HCID 9957292HCID 9957292, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of methyl 3,5-dibromo-4-(4-hydroxy-3-isopropylphenylsulfonyl)phenylacetate (2.7 g, 0.0053 mol), from Example 2, in 30 mL sodium hydroxide (5%) was heated at 60° C. for 10 min. The reaction mixture was cooled and extracted with ethyl acetate. The aqueous phase was acidified with hydrochloric acid (6N) and extracted with ethyl acetate (2X). The combined extract was washed with water and brine and dried (Na2SO4). The residue obtained after removal of the solvent was crystallized from hexane-ethyl acetate to obtain 3,5-dibromo-4-(4-hydroxy-3-isopropylphenylsulfonyl)phenylacetic acid (2.5 g, 0.0051 mol, 96% yield), MP: 171°-172° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionextracted with ethyl acetate (2X)
  4. extractionThe combined extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customThe residue obtained
  8. customafter removal of the solvent
  9. customwas crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-457d0059e47c49aea933e66dee817bf7
Source dataset
uspto-grants-1994_02
Patent number
US05284971

Reaction notes

Loading…