Hydrochloric Acid → 4-Bromo-7-fluoroindan-1-one

HRID 536472노트

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HRID 536472 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[C:13](=[O:15])[CH2:12][CH2:11]2.[Br:16]Br.Cl>ClC(Cl)C>[Br:16][C:9]1[CH:8]=[CH:7][C:6]([F:5])=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 27827677-Fluoroindan-1-oneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 534401624-Bromo-7-fluoroindan-1-one수율 64.3%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

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온도
65 °C

실험 절차

To a room temperature solution of aluminum chloride (11.77 g, 88 mmol) in dichloroethane (100 mL) was added 7-fluoro-2,3-dihydro-1H-inden-1-one (5.3 g, 35.3 mmol) followed with bromine (1.91 mL, 37.1 mmol). The mixture was heated at 65° C. for 16 hours, then cooled to ambient temperature and poured into a mixture of ice and HCl (1N aqueous). The mixture was extracted twice with ether (200 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes) to provide the title compound (5.2 g, 64%). MS (DCI/NH3) m/z 246 (M+NH4)+.

후처리

  1. temperaturecooled to ambient temperature
  2. extractionThe mixture was extracted twice with ether (200 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-cbf7ecc7154641d7ad6ef131b453762e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859584B2

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