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

HRID 415215

Reaktionsgleichung

Reaktionsgleichung von HRID 415215
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3190184a3dba4f93be2ec8e2fc80135e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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