Chlorosuccinimide → Ethyl 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

HRID 1510437노트

반응식

HRID 1510437 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=2)=[CH:5][CH:4]=1.[Cl:21]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:21][C:10]1[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][O:13][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 31398Chlorosuccinimide2회HCID 22064085Ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

생성물 1

HCID 67121079Ethyl 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate수율 86.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
75 °C

실험 절차

To a suspension of ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate (3.3 g, 11.6 mmol) in acetic acid (60 mL) was added N-chlorosuccinimide (3.1 g, 23.2 mmol). Upon heating to 75° C., a homogenous solution formed. After heating for 16 hours a further portion of N-chlorosuccinimide (1.5 g, 11.2 mmol) was added and the reaction was heated at 75° C. for another 16 hours. After cooling to ambient temperature, the reaction mixture was poured over ice. The white crystals which formed were collected by vacuum filtration and purified by silica gel chromatography, eluting with dichloromethane to obtain the title compound (3.2 g, 10.0 mmol).

후처리

  1. customa homogenous solution formed
  2. additionwas added
  3. temperaturethe reaction was heated at 75° C. for another 16 hours
  4. temperatureAfter cooling to ambient temperature
  5. additionthe reaction mixture was poured over ice
  6. customThe white crystals which formed
  7. filtrationwere collected by vacuum filtration
  8. custompurified by silica gel chromatography
  9. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-79638dfe31f5444583a6460c472f400a
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211927B2

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