Hydrochloric Acid → Ethyl 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1-oxo-1H-indene-2-acetate

HRID 232540Notes

Reaction equation

HRID 232540 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:7]2.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 199754355-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 54264824Ethyl 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1-oxo-1H-indene-2-acetateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of 0.720 g (0.018 mol) of 60% sodium hydride suspended in 50 mL DMF at 10° C. was added dropwise 4.0 g (0.0164 mol) of the product from step B dissolved in 25 mL DMF. The reaction mixture was stirred at 10° C. for 20 min. and 3.1 g (0.0164 mol) ethyl bromoacetate was added all at once. The reaction was heated at 60° C. for 15 min, cooled to room temperature, poured into 200 mL 10% HCl, extracted with ethyl acetate (3×50 mL), washed with brine (1×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to afford 4.0 g of a viscous oil.

Workup

  1. temperatureThe reaction was heated at 60° C. for 15 min
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washwashed with brine (1×100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f14d0b38e354bc990deaf106b340fe8
Source dataset
uspto-grants-1997_01
Patent number
US05591729

Reaction notes

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