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

HRID 731668ノート

反応式

HRID 731668 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 5943Carbon Tetrachloride溶媒2 回

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-b2e60627a8294d0a8461175471cc4634
出典データセット
uspto-grants-2009_09
特許番号
US07585874B2

反応ノート

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