Bromine → 2-Bromo-1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone

HRID 731668노트

반응식

HRID 731668 반응식
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[C:15](=[O:17])[CH3:16])[CH2:3][CH2:2]1.[Br:18]Br>C(Cl)(Cl)(Cl)Cl.CC(O)=O>[Br:18][CH2:16][C:15]([C:5]1[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1)=[O:17]

참가 물질

5

반응물 2

HCID 24408BromineHCID 674211361-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone

생성물 1

HCID 247398072-Bromo-1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone수율 96%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 5943Carbon Tetrachloride용매2회

실험 절차

To a solution of 1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone (3.34 g, 14.6 mmol) in carbontetrachloride (9.7 mL) and AcOH (0.4 mL) at 48° C. was added a solution of bromine (0.79 mL, 14.6 mmol) in carbontetrachloride (7.8 mL) over 10 min keeping the temperature below 50° C. After addition the reaction mixture was allowed to cool down to room temperature and poured into ice-water (50 mL). The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 80:20) afforded the title compound (4.29 g, 95%) which was obtained as an off-white solid. MS m/e (EI): 305.0/307.0 [M].

후처리

  1. customthe temperature below 50° C
  2. additionAfter addition the reaction mixture
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane
  5. washThe combined organic layers were then washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 80:20)

출처 및 근거

ORD 기록
ord-b2e60627a8294d0a8461175471cc4634
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585874B2

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