Iodine → Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate

HRID 507026

Reaktionsgleichung

Reaktionsgleichung von HRID 507026
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:16]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[C:9]([I:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 2

HCID 807IodineHCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoate

Produkt 1

HCID 53436880Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418844HCID 178418844, VerbindungKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Add a solution of methyl 2-amino-4-trifluoromethylbenzoate (178 g, 812 mmol) in ethanol (3.3 L) to a suspension of iodine (206.1 g, 812 mmol) and silver (II) sulfate (253 g, 812 mmol) in ethanol (5 L) at room temperature under an atmosphere of nitrogen and stir for 2 h. Filter the suspension through a pad of a Celite®, wash the pad with additional ethanol (2 L) and remove the solvents from the combined filtrates under reduced pressure at 40° C. Dissolve the residue in ethyl acetate (7.5 L) and wash with saturated sodium bicarbonate solution (3×1.5 L), water (3×1.5 L) and brine (2 L). Dry the organic phase over anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure to give the title compound as a pale brown crystalline solid (276.0 g, 99%). 1H NMR (300 MHz, CDCl3) δ 8.39 (1H, s), 6.99 (1H, s), 5.93 (2H, s), 3.90 (3 H, s).

Aufarbeitung

  1. filtrationFilter the suspension through a pad of a Celite®
  2. washwash the pad with additional ethanol (2 L)
  3. customremove the solvents from the combined filtrates under reduced pressure at 40° C
  4. dissolutionDissolve the residue in ethyl acetate (7.5 L)
  5. washwash with saturated sodium bicarbonate solution (3×1.5 L), water (3×1.5 L) and brine (2 L)
  6. dry with materialDry the organic phase over anhydrous magnesium sulfate
  7. filtrationfilter
  8. customremove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fe593709d9aa4b6c9596f60987a1d004
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786108B2

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