Hydrogen Peroxide → 2-[6-Fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetic acid

HRID 377358

Reaction equation

HRID 377358 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:23])=[O:22])=[CH:17][CH:16]=1)[C:9]([CH3:24])=[C:8]2[CH2:25][C:26]([OH:28])=[O:27].C(=O)(O)[O-:30].[Na+].OO.[H][H]>CO.C(#N)C>[F:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:23])(=[O:30])=[O:22])=[CH:17][CH:16]=1)[C:9]([CH3:24])=[C:8]2[CH2:25][C:26]([OH:28])=[O:27]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 53525-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 1148662-[6-Fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetic acidYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

5-fluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenyl acetic acid is prepared by adding sodium methoxide (4.4M in MeOH, 68.5 ml, 0.3 mol) dropwise to a stirred, cooled mixture of 5-fluoro-2-methyl-1-(p-methylsulfmylbenzylidene)-3-indenyl acetic acid (100 g, 0.281 mol) in methanol (250 ml) and acetonitrile (500 ml). Sodium bicarbonate (0.56 mol) and hydrogen peroxide (30% in water, 0.56 mol) are added and allowed to react for 18 hours at -10° C. Excess sodium bicarbonate is filtered off, and cooled filtrate (0° C.) neutralized dropwise to pH 7 with 1M hydrochloric acid (350 ml). The resulting product is then filtered and washed with methanol. A thin layer chromatography system to check for purity utilizes chloroform:methyl isobutyl ketone (8:2); the Rf value is 0.21. A tetrahydrofuran/diisopropyl ether combination can be used for product recrystallization. Reaction yield is 89%. (R1 =5-fluoro; R2 =CH3 ; R3 =hydrogen; R4 =COOH; R5 =CH3SO2; n=1).

Workup

  1. temperaturecooled
  2. customto react for 18 hours at -10° C
  3. filtrationExcess sodium bicarbonate is filtered off
  4. filtrationThe resulting product is then filtered
  5. washwashed with methanol
  6. customA tetrahydrofuran/diisopropyl ether combination can be used for product recrystallization
  7. customReaction yield is 89%

Sources & evidence

ORD record
ord-50dc758d57c14507902095155473aa6c
Source dataset
uspto-grants-2000_02
Patent number
US06025394

Linked notes

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