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Water → 1-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

HRID 1023850
ノート
印刷プレビュー

反応式

HRID 1023850 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.S(Cl)([Cl:15])(=O)=O.O>C(O)(=O)C>[Cl:15][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:11])=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=1.[Cl:15][C:3]1[C:4]([OH:11])=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 27373264'-Fluoro-2'-hydroxyacetophenone

生成物 2

HCID 162214361-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanoneHCID 672052361-(3-Chloro-4-fluoro-2-hydroxyphenyl)ethan-1-one

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °C

実験手順

To 1-(4-fluoro-2-hydroxyphenyl)ethanone (1.7 g, 11.03 mmol) in glacial acetic acid (24 mL) at 10° C. was slowly added sulfuryl chloride (2.23 g, 16.54 mmol). The mixture was heated to 120° C. and was allowed to stir for overnight. The solution was cooled down to room temperature and poured into water (30 mL). The water layer was extracted with EtOAc for three times. The EtOAc was washed with satd. Aq NaHCO3, water, brine, dried (Na2SO4) and concentrated recrystallized The mix was purified by column chromatography using 1:10 Hexanes:Ethyl acetate to yield 234 mg of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone and 400 mg of 1-(3-chloro-4-fluoro-2-hydroxyphenyl)ethanone. These compounds were used in the next step without characterization.

後処理

  1. customat 10° C.
  2. temperatureThe solution was cooled down to room temperature
  3. extractionThe water layer was extracted with EtOAc for three times
  4. washThe EtOAc was washed with satd
  5. dry with materialAq NaHCO3, water, brine, dried (Na2SO4)
  6. concentrationconcentrated
  7. customrecrystallized The mix
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-291ab45ed0594c0eb9c6f024e2e881dc
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722720B2

反応ノート

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