N-Iodosuccinimide → Ethyl 4-iodo-5-phenylisoxazole-3-carboxylate

HRID 1948457Notes

Reaction equation

HRID 1948457 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:17]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[I:17][C:8]1[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][O:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 571142Ethyl 5-phenylisoxazole-3-carboxylate

Product 1

HCID 58537206Ethyl 4-iodo-5-phenylisoxazole-3-carboxylateYield 152.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Large Scale: A mixture of ethyl 5-phenylisoxazole-3-carboxylate (3.05 g, 14.0 mmol) and N-iodosuccinimide (3.79 g, 16 9 mmol) in trifluoroacetic acid (78 mL) was stirred at room temperature for 3.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was washed with a 1N aqueous solution of sodium hydroxide (150 mL), washed with a 3% aqueous solution of sodium bisulfate (2×150 mL), washed with brine (150 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (4.69 g, 13.7 mmol, 97% yield) as a light yellow oil.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (150 mL) and water (150 mL)
  3. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide (150 mL)
  4. washwashed with a 3% aqueous solution of sodium bisulfate (2×150 mL)
  5. washwashed with brine (150 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-435c688f03644f3c828025655b39809e
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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