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

HRID 2388175ノート

反応式

HRID 2388175 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-dedcbfe9549c404bba354c973a9d351f
出典データセット
uspto-grants-2012_09
特許番号
US08269008B2

反応ノート

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