Chlorine → 2-Thiophenecarboxaldehyde, 4,5-dichloro-

HRID 1701333ノート

反応式

HRID 1701333 の反応式
[Cl:1][C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[Cl-:9].[Al+3].[Cl-].[Cl-].ClCl>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Cl:9][C:3]1[CH:4]=[C:5]([CH:7]=[O:8])[S:6][C:2]=1[Cl:1]

参加物

6

反応物 3

HCID 24526Chlorine2 回HCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 1494242-Thiophenecarboxaldehyde, 4,5-dichloro-

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a mechanically stirred solution of 31.8 grams (0.217 mole) 5-chloro-2thiophenecarboxaldehyde in 150 ml of methylene chloride, 65 grams (0.487 mole) of anhydrous aluminum chloride was added in small portions. The mixture exothermed and turned purple. To this mixture 20.6 grams (0.29 mole) of chlorine in 250 ml of carbon tetrachloride was added dropwise. The reaction mass was refluxed for about 15 hours, and an additional 15 grams (0.21 mole) of chlorine in 200 ml of carbon tetrachloride was added. The mixture was refluxed for an additional 7 hours. The reaction was quenched by pouring over one liter of ice water. The aqueous layer was extracted with chloroform. The chloroform solution was washed with water and sodium bicarbonate. After drying with anhydrous sodium sulfate and concentration under vacuum, a yellow-brown oil was obtained. The crude 4,5-dichloro-2-thiophenecarboxaldehyde crystallized on standing and was recrystallized from hexane.

後処理

  1. temperatureThe reaction mass was refluxed for about 15 hours
  2. temperatureThe mixture was refluxed for an additional 7 hours
  3. customThe reaction was quenched
  4. additionby pouring over one liter of ice water
  5. extractionThe aqueous layer was extracted with chloroform
  6. washThe chloroform solution was washed with water and sodium bicarbonate
  7. dry with materialAfter drying with anhydrous sodium sulfate and concentration under vacuum
  8. customa yellow-brown oil was obtained
  9. customThe crude 4,5-dichloro-2-thiophenecarboxaldehyde crystallized
  10. customwas recrystallized from hexane

出典と根拠

ORDレコード
ord-173897e50ca64886aa8fcc8ea84207e5
出典データセット
uspto-grants-1980_03
特許番号
US04192884

反応ノート

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