Nitric Acid → 2-Bromo-5-fluoro-3-nitrobenzoic acid

反応式

OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[Br:10][C:11]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>>[Br:10][C:11]1[C:19]([N+:6]([O-:9])=[O:7])=[CH:18][C:17]([F:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

参加物

反応物 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 27781812-Bromo-5-fluorobenzoic acid

生成物 1

HCID 185485832-Bromo-5-fluoro-3-nitrobenzoic acid収率 49%

実験手順

To a 3 liter round bottom flask was charged with 500 ml H2SO4. Fuming nitric acid was added (40 mL) and the mixture gently stirred. 2-Bromo-5-fluorobenzoic acid (60 g, 219 mmol) was added in 5 g portions over 90 minutes at 5-10° C. The mixture was stirred for 60 minutes at which time the reaction was completed. The mixture was poured into 1 liter of an ice/water mixture and extracted with EtOAc (3×600 mL). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid was suspended in hexanes and stirred for 30 minutes. The solid was collected on filter to provide 2-bromo-5-fluoro-3-nitrobenzoic acid as yellow solid (35 g, 49%).