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

HRID 1804448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804448
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 58537206Ethyl 4-iodo-5-phenylisoxazole-3-carboxylateAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

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 bisulfite (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.

Aufarbeitung

  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 bisulfite (2×150 mL)
  5. washwashed with brine (150 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a231e88e94a845019c2b19e57e549d25
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354398B2

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