Nitric Acid → 1-Iodo-2-nitro-4-(trifluoromethyl)benzene
Reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[F:10][C:11]([F:20])([F:19])[C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=1>O>[N+:6]([C:14]1[CH:13]=[C:12]([C:11]([F:19])([F:20])[F:10])[CH:17]=[CH:16][C:15]=1[I:18])([O-:9])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 87.6 ml of concentrated sulphuric acid and 46.8 ml of concentrated nitric acid (d=1.52) is prepared at 0° C. This mixture is added dropwise to 272 g of p-trifluoromethyliodobenzene maintained at 50° C., which takes about 1 hour, after which time the application of heat is ceased and stirring is continued for a further 30 minutes. The mixture is then hydrolysed by pouring onto 750 ml of water. The product is subsequently extracted three times with 600 ml of dichloromethane each time, and the organic phase is washed in succession with water and a 20% solution of sodium bicarbonate. The solvent is then evaporated and distillation yields 273 g of 2-nitro-4-trifluoromethyliodobenzene, b.p./8 mm =120°-125° C. (yield 86%).
Workup
- customis prepared at 0° C
- temperatureafter which time the application of heat
- waitis continued for a further 30 minutes
- extractionThe product is subsequently extracted three times with 600 ml of dichloromethane each time
- washthe organic phase is washed in succession with water
- customThe solvent is then evaporated
- distillationdistillation
Sources & evidence
- ORD record
- ord-902a181fa60641ed8e81f9d75755488d
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05079245
Reaction notes
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