Water → 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one

HRID 232539Notes

Reaction equation

HRID 232539 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.O>CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:10](=[O:12])[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH2:8]2

Participants

4

Reactant 2

HCID 962WaterHCID 233587593-Fluoro-alpha-(4-fluorophenyl)-benzenepropanoic acid

Product 1

HCID 199754355-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 500 g of polyphosphoric acid was heated to 60° C. and 43.0 g of the acid from step A was added. The mixture was then heated to 110° C. for 1 hour. After this time, the reaction was cooled to about 60° C. and 400 mL of water was added rapidly with external cooling. The mixture was then partitioned between toluene and water, washed twice with toluene and the combined toluene extracts were then washed with 5% aqueous NaHCO3. The toluene extracts were then dried over MgSO4, filtered, concentrated and chromatographed on silica gel with 10% ethyl acetate in hexane as the eluent to afford, after trituration with hexane, 26.98 g of a yellow solid; mp 72°-74° C.

Workup

  1. temperatureAfter this time, the reaction was cooled to about 60° C.
  2. customThe mixture was then partitioned between toluene and water
  3. washwashed twice with toluene
  4. washthe combined toluene extracts were then washed with 5% aqueous NaHCO3
  5. dry with materialThe toluene extracts were then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel with 10% ethyl acetate in hexane as the eluent
  9. customto afford

Sources & evidence

ORD record
ord-940508cfe7b94d099d21ea6ce8860578
Source dataset
uspto-grants-1997_01
Patent number
US05591729

Reaction notes

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