Chlorosuccinimide → Ethyl 5-(4-tert-butylphenyl)-4-chloroisoxazole-3-carboxylate

HRID 1510460Notes

Reaction equation

HRID 1510460 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:21]N1C(=O)CCC1=O>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]=2[Cl:21])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20534825Ethyl 5-(4-tert-butylphenyl)-1,2-oxazole-3-carboxylate

Product 1

HCID 67121140Ethyl 5-(4-tert-butylphenyl)-4-chloroisoxazole-3-carboxylateYield 35.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 5-(4-tert-butylphenyl)isoxazole-3-carboxylate (2.0 g, 7.32 mmol) and N-chlorosuccinimide (2.44 g, 18.3 mmol) in acetic acid (50 mL) was heated to reflux for 3 days. The reaction mixture was then allowed to cool to room temperature, poured over ice and the resulting white solid was collected, dissolved in ethyl acetate and the organics washed with water, brine and dried with sodium sulphate before being filtered, and evaporated in vacuo. The resultant residue was re-dissolved in dichloromethane, this was then extracted with sodium carbonate solution, and dried using a hydrophobic frit. The organics were removed in vacuo to obtain ethyl 5-(4-tert-butylphenyl)-4-chloroisoxazole-3-carboxylate (0.81 g, 2.63 mmol).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. additionpoured over ice
  4. customthe resulting white solid was collected
  5. dissolutiondissolved in ethyl acetate
  6. washthe organics washed with water, brine
  7. dry with materialdried with sodium sulphate
  8. filtrationbefore being filtered
  9. customevaporated in vacuo
  10. dissolutionThe resultant residue was re-dissolved in dichloromethane
  11. extractionthis was then extracted with sodium carbonate solution
  12. customdried
  13. customThe organics were removed in vacuo

Sources & evidence

ORD record
ord-7239fe33a3734dda91aee15b419968d2
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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