N-bromobutanimide → Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415215

反応式

HRID 415215 の反応式
[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=1.[Br:21]N1C(=O)CCC1=O.C(OO)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:21][CH2:20][C:1]1[CH:2]=[C:3]([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 523077Perbenzoic acidHCID 66620979Methyl 2-m-tolylbenzo[d]oxazole-7-carboxylate

生成物 1

HCID 66620978Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate収率 30%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Methyl 2-m-tolylbenzo[d]oxazole-7-carboxylate (500 mg, 1.87 mmol), 1-bromopyrrolidine-2,5-dione (367 mg, 2.06 mmol) and benzoperoxoic acid (25.81 mg, 0.187 mmol) were added to toluene (30 mL) and the mixture was stirred at reflux overnight. The resulting mixture was evaporated, extracted with ethyl acetate (100 mL×4) and concentrated to obtain methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate as a solid (194 mg, yield 30%). LC-MS (ESI) m/z 347 [M+1]+.

後処理

  1. temperatureat reflux overnight
  2. customThe resulting mixture was evaporated
  3. extractionextracted with ethyl acetate (100 mL×4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-3190184a3dba4f93be2ec8e2fc80135e
出典データセット
uspto-grants-2012_01
特許番号
US08088760B2

関連ノート

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