Ethyl Acetate → 2,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline
Reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].F[C:21]1[C:26]([F:27])=[C:25]([F:28])[CH:24]=[C:23]([F:29])[C:22]=1[N+:30]([O-:32])=[O:31].C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]1[C:22]([N+:30]([O-:32])=[O:31])=[C:23]([F:29])[CH:24]=[C:25]([F:28])[C:26]=1[F:27]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A stirred solution of 2-fluoro-4-iodoaniline (3.64 gm, 15.37 mmol) in dry THF (100 ml) under nitrogen was cooled to −78° C. and a solution of 1.0 M lithium hexamethyl disilazide (LiN(SiMe3)2) “LHMDS” (15.37 ml, 15.37 mmol) was added slowly. This reaction mixture was stirred at −78° C. for another hour, and then 2,3,4,6-tetrafluoronitrobenzene was added. The reaction mixture was allowed to warm to room temperature, and stirring continued for another 16 hours. Ethyl acetate (200 mL) was added to the reaction mixture, and the mixture was washed with water. The organic layer was dried over sodium sulfate and further purified by column chromatography to provide yellow solid (3.75 gm, yield: 59.24%).
Workup
- temperatureto warm to room temperature
- stirringstirring
- washthe mixture was washed with water
- dry with materialThe organic layer was dried over sodium sulfate
- customfurther purified by column chromatography
Sources & evidence
- ORD record
- ord-b385b6d2e2d14e848709c77bc868af63
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842836B2
Reaction notes
Loading…