Acetic Acid → 2',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid
Reaktionsgleichung
[CH:1]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([F:14])=[CH:11][C:12]=2[F:13])=[CH:5][C:4]([C:15]([OH:17])=[O:16])=[C:3]([OH:18])[CH:2]=1.[Na+].[I-:20].C(O)(=O)C>C(#N)C>[F:13][C:12]1[CH:11]=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:6]1[CH:5]=[C:4]([C:15]([OH:17])=[O:16])[C:3]([OH:18])=[C:2]([I:20])[CH:1]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
20 mg (0.08 mmol) of diflunisal, 14 mg (0.093 mmol) of NaI and 30 mg (0.13 mmol) of CAT dissolved in 1040 μl of acetonitrile and 52 μl of acetic acid are placed in a 25 ml flask. It was stirred for 1.5 hr at room temperature. The reaction was monitored by HPLC until the consumption of starting product was observed and 96% of iodinated product was detected. The solution was then acidified to pH=1.0 with a 5% solution of HCl and extracted with ethyl acetate. The organic phases were combined and washed with a solution of sodium thiosulphate and then dried over anhydrous magnesium sulphate. The solvent was removed at low pressure and a crude of 98% purity was obtained and then purified by chromatography on silica gel. 260 mg (86% yield) of the desired product was obtained.
Aufarbeitung
- customThe reaction was monitored by HPLC until the consumption of starting product
- extractionextracted with ethyl acetate
- washwashed with a solution of sodium thiosulphate
- dry with materialdried over anhydrous magnesium sulphate
- customThe solvent was removed at low pressure
- customa crude of 98% purity was obtained
- custompurified by chromatography on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-abb00b51bc254686b08b181c5cf5e3f6
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07265245B2
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