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

HRID 547658노트

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HRID 547658 반응식
[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

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 575859753-(3,4-Difluorophenyl)propanoyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매2회

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f8e6ac3b4f0e41cab5c08dca2293e2ae
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939528B2

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