N-bromobutanimide → Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylate

HRID 1651698

反応式

HRID 1651698 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>O1CCCC1>[Br:18][C:12]1[NH:11][CH:10]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 470434ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylate

生成物 1

HCID 15010185Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylate収率 90,348.398%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 4-(p-chlorophenyl)pyrrole-3-carboxylate (1.6 g., 0.0064 mmol) is dissolved in tetrahydrofuran (40 mL). N-bromosuccinimide (1.14 g., 0.0064 mmol) is added in small portions at 25°-28° C. After the addition is complete, the solution is stirred overnight at room temperature. The solution is concentrated in vacuo and the solid residue partioned between water and ether. The ether layer is separated and dried over magnesium sulfate. Work-up of the ether extract leaves 1.9 g (90%) of a white solid which is purified by stirring with a mixture of 80/20 hexane/ethyl acetate. The insoluble solid (1.3 g, 62%) is collected and has m.p. 161°-164° C.

後処理

  1. additionAfter the addition
  2. concentrationThe solution is concentrated in vacuo
  3. customThe ether layer is separated
  4. dry with materialdried over magnesium sulfate
  5. extractionextract

出典と根拠

ORDレコード
ord-fc130aedf3ed4b838c554581ebb01c08
出典データセット
uspto-grants-1990_05
特許番号
US04929634

関連ノート

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