N-bromobutanimide → Ethyl 4-(bromomethyl)-3-(4-fluorophenyl)isoxazole-5-carboxylate

HRID 2388175노트

반응식

HRID 2388175 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:13][C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][O:10][C:11]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 67530024Ethyl 3-(4-fluorophenyl)-4-methylisoxazole-5-carboxylate

생성물 1

HCID 67529002Ethyl 4-(bromomethyl)-3-(4-fluorophenyl)isoxazole-5-carboxylate수율 109.5%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

Ethyl 3-(4-fluorophenyl)-4-methylisoxazole-5-carboxylate (8.6 g, 34.5 mmol), NBS (6.8 g, 38.0 mmol), and benzoyl peroxide (0.84 g, 3.45 mmol) were added to 200 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The reaction mixture was filtered and the filtrate was removed in vacuo to give 12.4 g of the title compound. 1H NMR (CDCl3, 200 MHz): δ=9.21 (s, 1H), 7.75-7.85 (m, 2H), 7.22-7.32 (m, 2H), 4.66 (s, 2H), 4.54 (q, 2H, J=7.0 Hz), 1.41 (t, 3H, J=7.0 Hz).

후처리

  1. temperaturethe mixture was refluxed for 16 h
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was removed in vacuo

출처 및 근거

ORD 기록
ord-dedcbfe9549c404bba354c973a9d351f
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269008B2

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