N-bromobutanimide → Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate

HRID 1510426ノート

反応式

HRID 1510426 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(O)(=O)C>[Br:18][C:9]1[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimide2 回HCID 13035537Ethyl 5-(4-chlorophenyl)-1,2-oxazole-3-carboxylate

生成物 1

HCID 67121165Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate収率 71.8%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of ethyl 5-(4-chlorophenyl)isoxazole-3-carboxylate (0.66 g, 2.62 mmol) and N-bromosuccinimide (0.93 g, 5.2 mmol) in acetic acid (12 mL) was heated to reflux for 24 hours. An additional portion of N-bromosuccinimide (0.5 g, 2.8 mmol) was added and the reaction refluxed another 16 h. The reaction mixture was allowed to cool to room temperature, poured over ice and the resulting white solid was collected and purified by silica gel chromatography, eluting with dichloromethane to obtain ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate (0.62 g, 1.88 mmol).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperaturethe reaction refluxed another 16 h
  4. additionpoured over ice
  5. customthe resulting white solid was collected
  6. custompurified by silica gel chromatography
  7. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-ef53c0bb261c49f887902c79e40cf3ba
出典データセット
uspto-grants-2012_07
特許番号
US08211927B2

反応ノート

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