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

HRID 1033583

반응식

HRID 1033583 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ad8d558a86874856becc73421c1a1ec8
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310938

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