p-Toluenesulfonic acid → Ethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)acetate

HRID 2232635ノート

反応式

HRID 2232635 の反応式
[Br:1][C:2]1[C:3]([Cl:23])=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([CH:7](C(OCC)=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Br:1][C:2]1[C:3]([Cl:23])=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 14071798Diethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)malonate

生成物 1

HCID 14071799Ethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)acetate収率 48.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an emulsion of diethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)malonate (11.44 g) in water (16 ml) was added p-toluenesulfonic acid (15 mg) and refluxed for 3 hours with stirring vigorously. After cooling, the reaction mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with dichloromethane-n-hexane (1:1) to give the title compound (4.56 g), mp 47°-51° C.

後処理

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with dichloromethane-n-hexane (1:1)

出典と根拠

ORDレコード
ord-6e7b985b56334e989f4dd9c101437b89
出典データセット
uspto-grants-1988_11
特許番号
US04788320

反応ノート

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