N-bromobutanimide → 7-(4-Chlorophenoxy)isocoumarin

HRID 1609602ノート

反応式

HRID 1609602 の反応式
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:17]=[C:16]3[C:10]([CH2:11][CH2:12][O:13][C:14]3=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:17]=[C:16]3[C:10]([CH:11]=[CH:12][O:13][C:14]3=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 200820007-(4-Chlorophenoxy)-3,4-dihydroisocoumarin

生成物 1

HCID 200820017-(4-Chlorophenoxy)isocoumarin収率 73.9%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A solution of 500 mg of 7-(4-chlorophenoxy)-3,4-dihydroisocoumarin, 325 mg of N-bromosuccinimide and 20 mg of benzoyl peroxide in 20 ml of carbon tetrachloride was refluxed under heating for 2 hours. After finishing the reaction, the mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was mixed with 10 ml of toluene and 490 mg of 1,8-diazabicyclo[5, 4, 0]undec-7-ene and stirred at room temperature for 1 hour. The toluene was evaporated in vacuo, and the resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (1:1) to give 367 mg of the titled compound.

後処理

  1. temperatureunder heating for 2 hours
  2. customthe reaction
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe resultant residue was mixed with 10 ml of toluene and 490 mg of 1,8-diazabicyclo[5, 4, 0]undec-7-ene
  7. customThe toluene was evaporated in vacuo
  8. customthe resultant residue was chromatographed on a column of silica gel
  9. washeluting with ethyl acetate and hexane (1:1)

出典と根拠

ORDレコード
ord-d4959f0808cf473d882b26843b5d4a52
出典データセット
uspto-grants-1995_03
特許番号
US05401756

反応ノート

読み込み中…