N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415203Notes

Reaction equation

HRID 415203 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([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:3][CH:2]=1.C1C(=O)N([Br:28])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:20][C:1]1[CH:2]=[CH:3][C:4]([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:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66621103Methyl 2-p-tolylbenzo[d]oxazole-7-carboxylate

Product 1

HCID 66621208Methyl 2-(4-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylateYield 77.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of methyl 2-p-tolylbenzo[d]oxazole-7-carboxylate (1 g, 3.74 mmol) in CCl4 (7 mL) was added NBS (665 mg, 3.74 mmol) and BPO (52 mg, 0.37 mmol), heated to reflux for 24 hr, then the solvent was evaporated, and purified by silica gel chromatography (petroleum ether:ethyl acetate=100:1-50:1) to obtain methyl 2-(4-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate as a white solid (1.0 g, yield 77%). LC-MS (ESI) m/z 346 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hr
  3. customthe solvent was evaporated
  4. custompurified by silica gel chromatography (petroleum ether:ethyl acetate=100:1-50:1)

Sources & evidence

ORD record
ord-c2cfc628148d4ed4a00d92274e993263
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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