Iodine → 2-Amino-4-difluoromethyl-5-iodo-benzoic acid methyl ester

HRID 1894099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894099
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([F:12])[F:11])=[CH:6][C:5]=1[NH2:13].[I:15]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([I:15])[C:7]([CH:10]([F:12])[F:11])=[CH:6][C:5]=1[NH2:13]

Komponenten

5

Edukt 2

HCID 807IodineHCID 591644252-Amino-4-difluoromethyl-benzoic acid methyl ester

Produkt 1

HCID 591644452-Amino-4-difluoromethyl-5-iodo-benzoic acid methyl esterAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159865Silver sulfateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4-difluoromethyl-benzoic acid methyl ester (1.98 g, 9.84 mmol) in EtOH (75 mL) were added Ag2SO4 (3.08 g, 1 equiv) and I2 (2.50 g, 1 equiv) and the resulting mixture was stirred at r.t. for 1 hour. The mixture was filtered through a pad of celite and washed with EtOH. The solution was concentrated in vacuo and then diluted with AcOEt. The organic phase was washed with sat. aq NaHCO3, 1M aq Na2S2O3 and brine and dried (Na2SO4). The solution was concentrated in vacuo to afford the title compound as an off-white solid (2.9 g, 90% yield). ES-MS: m/z 369.2 [M+CH3CN+H]+, rt 5.87 min.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashed with EtOH
  3. concentrationThe solution was concentrated in vacuo
  4. additiondiluted with AcOEt
  5. washThe organic phase was washed with sat. aq NaHCO3, 1M aq Na2S2O3 and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7f4664b3109d4d1bbd64e04913abf39c
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513268B2

Notizen zur Reaktion

Wird geladen…