2-(4-Fluorophenyl)acetic acid → HCID 21110619, compound

HRID 1766686Notes

Reaction equation

HRID 1766686 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][C:8]2[C:9]([CH3:26])=[CH:10][C:11]([NH:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]3[C:16]=2[CH2:15][CH2:14][CH2:13]3)=[CH:5][CH:4]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](O)=[O:38])=[CH:32][CH:31]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([C:4]2[CH:5]=[C:6]([CH:27]=[CH:28][C:3]=2[O:2][CH3:1])[O:7][C:8]2[C:9]([CH3:26])=[CH:10][C:11]([NH:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]3[C:16]=2[CH2:15][CH2:14][CH2:13]3)=[O:38])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 98372-(4-Fluorophenyl)acetic acidHCID 67749Trifluoromethanesulfonic anhydrideHCID 21110664HCID 21110664, compound

Product 1

HCID 21110619HCID 21110619, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl N-[7-(4-methoxyphenoxy)-6-methylindan-4-yl]malonamate (100 mg) and 4-fluorophenylacetic acid (60 mg) were dissolved in dichloromethane (261 μL). To the solution was added dropwise trifluoromethanesulfonic anhydride (66 μL) at room temperature with stirring. The mixture was stirred at room temperature for 15 hours. Adding water, the reaction mixture was extracted with diethyl ether. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give the title compound (74 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hours
  2. extractionAdding water, the reaction mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-3a341a7a7d7740ce8f221cf8dfef122c
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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