N-bromobutanimide → Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate

HRID 1510426Notes

Reaction equation

HRID 1510426 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(O)(=O)C>[Br:18][C:9]1[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 13035537Ethyl 5-(4-chlorophenyl)-1,2-oxazole-3-carboxylate

Product 1

HCID 67121165Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylateYield 71.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 5-(4-chlorophenyl)isoxazole-3-carboxylate (0.66 g, 2.62 mmol) and N-bromosuccinimide (0.93 g, 5.2 mmol) in acetic acid (12 mL) was heated to reflux for 24 hours. An additional portion of N-bromosuccinimide (0.5 g, 2.8 mmol) was added and the reaction refluxed another 16 h. The reaction mixture was allowed to cool to room temperature, poured over ice and the resulting white solid was collected and purified by silica gel chromatography, eluting with dichloromethane to obtain ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate (0.62 g, 1.88 mmol).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperaturethe reaction refluxed another 16 h
  4. additionpoured over ice
  5. customthe resulting white solid was collected
  6. custompurified by silica gel chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ef53c0bb261c49f887902c79e40cf3ba
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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