Water → 1,3-Difluoro-2-nitrobenzene
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].B1([O-])OO1.[OH2:14].[OH2:15].O.O.[Na+].O>C(O)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[N+:4]([O-:15])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
2,6-Difluoroaniline (11.0 g, 85 mmol) in glacial acetic acid (50 mL) was added slowly to a stirred suspension of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) at 80° C. The temperature was maintained between 80-90° C. for 1 hour. The cooled reaction mixture was poured into water and extracted twice with diethyl ether, the combined organic layers were washed with a dilute solution of sodium bicarbonate, dried (MgSO4) and evaporated. The residue was purified by silica gel column chromatography (Hexane:THF, 9:1) and the product washed with hexane to afford 2,6-difluoronitrobenzene (7.0 g) which was used without further examination.
Workup
- customThe cooled reaction mixture
- extractionextracted twice with diethyl ether
- washthe combined organic layers were washed with a dilute solution of sodium bicarbonate
- dry with materialdried (MgSO4)
- customevaporated
- customThe residue was purified by silica gel column chromatography (Hexane:THF, 9:1)
- washthe product washed with hexane
Sources & evidence
- ORD record
- ord-f2a596d847ed4e89b6b1d51d403718d8
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317037B2
Reaction notes
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