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

HRID 536472ノート

反応式

HRID 536472 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 534401624-Bromo-7-fluoroindan-1-one収率 64.3%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
65 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-cbf7ecc7154641d7ad6ef131b453762e
出典データセット
uspto-grants-2014_10
特許番号
US08859584B2

反応ノート

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