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

HRID 415215

반응식

HRID 415215 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-3190184a3dba4f93be2ec8e2fc80135e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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