Reaktion #40445

Reaktionsgleichung

5-fluoro-2-nitrobenzoic acid

2-amino-5-bromopyridine

phosphorous oxychloride

→

N-(5-bromo-2-pyridinyl)-(2-nitro)-5-fluorophenylcarboxamide

Ausbeute 68.1%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatile was evaporated
2. 2
   workup.DISSOLUTIONthe residue was redissolved into EtOAc
3. 3
   Waschen, washed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
4. 4
   TrocknenThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe volatile was evaporated
8. 8
   Sonstigethe product was triturated with diethyl ether

Vorschrift

A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv), 2-amino-5-bromopyridine (12.2 g, 1.3 equiv), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv) for 30 min. The volatile was evaporated and the residue was redissolved into EtOAc., washed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and evaporated. The volatile was evaporated, and the product was triturated with diethyl ether to give N-(5-bromo-2-pyridinyl)-(2-nitro)-5-fluorophenylcarboxamide (12.5 g, 68%). MS found for C12H7BrFN3O3 (M+H)+: 340, 342.

Quelle