Hydrochloric Acid → 4-bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

HRID 536463ノート

反応式

HRID 536463 の反応式
[Cl-].[Cl-].[Cl-].[Al+3].[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9]2.[Br:16]Br.Cl>ClC(Cl)C.C(OCC)C>[Br:16][C:7]1[C:6]([F:5])=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[O:15]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 1365375-Fluoro-1-indanoneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 666462974-bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 63651,1-Dichloroethane溶媒2 回

反応条件

温度
70 °C

実験手順

A solution of aluminum trichloride (11.10 g, 83.00 mmol) in dichloroethane (100 mL) was slowly added a solution of 5-fluoro-2,3-dihydro-1H-inden-1-one (5 g, 33.3 mmol) in dichloroethane (10 mL) at ambient temperature and stirred for 5 minutes, followed with the addition of bromine (2.57 mL, 50.0 mmol). The resulting dark red mixture was heated at 70° C. for 2 hours. The reaction mixture was cooled to ambient temperature and poured into a mixture of ice and HCl (1N, 50 mL). Diethyl ether (300 mL) was added and the mixture was partitioned. The organic portion was washed with water (75 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (gradient elution: 0-10% EtOAc/hexanes) to provide the title compound mixed with inseparable bisbrominated side product (4,7-dibromo-5-fluoro-2,3-dihydro-1H-inden-1-one). MS (DCI) m/z 246 (M+NH4)+.

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe mixture was partitioned
  3. washThe organic portion was washed with water (75 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was chromatographed on silica gel (gradient elution: 0-10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-6fb9c2ae02e44af0a655a526911a154b
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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