Hydrochloric Acid → 4-(o-Fluorobenzoyl)-5-methoxybenzocyclobutene-1-carboxylic acid methyl ester

HRID 1248360ノート

反応式

HRID 1248360 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].Cl>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([O:13][CH3:14])[C:11]([C:22](=[O:23])[C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[F:19])=[CH:12][C:7]=2[CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

生成物 1

HCID 1784969314-(o-Fluorobenzoyl)-5-methoxybenzocyclobutene-1-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

While stirring at from 0 to 3°, 9.61 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester are added dropwise to a suspension, cooled to 0°, of 26.6 g of aluminium trichloride in 60 ml of dichloromethane. The whole is stirred for 30 minutes at 0°, 15.9 g of o-fluorobenzoyl chloride are added dropwise thereto and stirring is carried out for 2 hours at from 0° to 3°. The whole is then poured into a mixture of 100 g of ice-water and 5 ml of concentrated hydrochloric acid, extracted by shaking twice with 100 ml of dichloromethane each time, washed with water, dried over magnesium sulphate and concentrated to dryness by evaporation. The residue is taken up in a small amount of dichloromethane, petroleum ether is added until a precipitate begins to form and the whole is then cooled. The precipitate that has formed is filtered off with suction and the filtrate is concentrated by evaporation and chromatographed over silica gel using dichloromethane as eluant. After a small number of first runnings, 4-(o-fluorobenzoyl)-5-methoxybenzocyclobutene-1-carboxylic acid methyl ester is obtained having a melting point of 73°-74°.

後処理

  1. additionare added dropwise to a suspension
  2. stirringstirring
  3. waitis carried out for 2 hours at from 0° to 3°
  4. extractionextracted
  5. stirringby shaking twice with 100 ml of dichloromethane each time
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness by evaporation
  9. additionis added until a precipitate
  10. customto form
  11. temperaturethe whole is then cooled
  12. customThe precipitate that has formed
  13. filtrationis filtered off with suction
  14. concentrationthe filtrate is concentrated by evaporation
  15. customchromatographed over silica gel

出典と根拠

ORDレコード
ord-5f4cabec03b242e0941c64a2f7360194
出典データセット
uspto-grants-1985_06
特許番号
US04523030

反応ノート

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