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

HRID 1510426노트

반응식

HRID 1510426 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(O)(=O)C>[Br:18][C:9]1[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimide2회HCID 13035537Ethyl 5-(4-chlorophenyl)-1,2-oxazole-3-carboxylate

생성물 1

HCID 67121165Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate수율 71.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of ethyl 5-(4-chlorophenyl)isoxazole-3-carboxylate (0.66 g, 2.62 mmol) and N-bromosuccinimide (0.93 g, 5.2 mmol) in acetic acid (12 mL) was heated to reflux for 24 hours. An additional portion of N-bromosuccinimide (0.5 g, 2.8 mmol) was added and the reaction refluxed another 16 h. The reaction mixture was allowed to cool to room temperature, poured over ice and the resulting white solid was collected and purified by silica gel chromatography, eluting with dichloromethane to obtain ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate (0.62 g, 1.88 mmol).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperaturethe reaction refluxed another 16 h
  4. additionpoured over ice
  5. customthe resulting white solid was collected
  6. custompurified by silica gel chromatography
  7. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-ef53c0bb261c49f887902c79e40cf3ba
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211927B2

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