Bromoacetonitrile → 4-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyronitrile

HRID 11728

反応式

HRID 11728 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.COC(=O)[O-].[Mg+2].COC(=O)[O-].Br[CH2:24][C:25]#[N:26]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH2:9][CH2:24][C:25]#[N:26])[CH:7]=1

参加物

5

反応物 3

HCID 11534BromoacetonitrileHCID 740613-Chloro-6-hydroxyacetophenoneHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

生成物 1

HCID 219733224-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyronitrile収率 58.6%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A solution of 1-(5-chloro-2-hydroxy-phenyl)-ethanone (1.0 g, 5.86 mmol) and magnesium methylcarbonate (13 mL, 32.5 mmol, 2.5 M solution in DMF) was stirred at 120° C. for 3 hours. The mixture was cooled to ambient temperature followed by the addition of bromoacetonitrile (1.22 mL, 17.6 mmol). The resulting solution was stirred at 90° C. for 3 hours. The reaction was cooled to ambient temperature then slowly poured into 1 M hydrochloric acid (200 mL). This was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered and concentrated. Flash chromatography on silica gel gave the title compound (0.72 g).

後処理

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionThis was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-17531f7d84eb482b9d2cd0545ab98c03
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

関連ノート

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