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

HRID 415215

Reaction equation

HRID 415215 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-3190184a3dba4f93be2ec8e2fc80135e
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Linked notes

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