N-bromobutanimide → Ethyl 5-(bromomethyl)-2-phenyl-1,3-oxazole-4-carboxylate

HRID 453291Notes

Reaction equation

HRID 453291 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3231335Ethyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate

Product 1

HCID 12868788Ethyl 5-(bromomethyl)-2-phenyl-1,3-oxazole-4-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl 5-methyl-2-phenyloxazole-4-carboxylate (11.0 g, 48 mmol), NBS (8.5 g, 48 mmol), and BPO (100 mg) in CCl4 (200 ml) was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography to give ethyl 5-(bromomethyl)-2-phenyloxazole-4-carboxylate as a tan solid (5.2 g, 35% yield).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c6d9ffb346a1478090bc602b7ad56159
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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