Aluminum(III) Chloride → 5,6-Difluoro-1-indanone

HRID 547658Notes

Reaction equation

HRID 547658 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][C:15](Cl)=[O:16])[CH:9]=[CH:10][C:11]=1[F:12]>C(=S)=S>[F:5][C:6]1[CH:7]=[C:8]2[C:9](=[CH:10][C:11]=1[F:12])[C:15](=[O:16])[CH2:14][CH2:13]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 575859753,4-Difluorobenzenepropanoyl chloride

Product 1

HCID 117689445,6-Difluoro-1-indanoneYield 70.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a carbon disulfide solution (300 mL) containing AlCl3 (76.4 g, 572.6 mmol) at 0° C. was added a carbon disulfide solution (120 mL) of 3-(3,4-difluorophenyl)propanoyl chloride (33.4 g, 163.6 mmol) over 10 min. The solution was stirred for 30 min at 0° C. and heated to reflux for 4 hours. Upon cooling to room temperature the solution was carefully poured onto crushed ice. The carbon disulfide layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent removed in vacuo. The residual solid was purified by silica gel column chromatography (5-10% ethyl acetate/hexanes) yielding 19.3 g (114.9 mmol, 70% yield) of 5,6-difluoro-2,3-dihydro-1H-inden-1-one as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.50 (t, 1H, J=8.0 Hz), 7.24 (t, 1H, J=6.6 Hz), 3.09 (t, 2H, J=5.5 Hz), 2.72-2.69 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureUpon cooling to room temperature the solution
  4. additionwas carefully poured
  5. customonto crushed ice
  6. customThe carbon disulfide layer was separated
  7. extractionthe aqueous layer extracted with ethyl acetate
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. customthe solvent removed in vacuo
  10. customThe residual solid was purified by silica gel column chromatography (5-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f8e6ac3b4f0e41cab5c08dca2293e2ae
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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