4-Bromo-2,6-difluoroaniline → 5-Bromo-1,3-difluoro-2-nitrobenzene
Reaction equation
B1([O-])OO1.[OH2:5].[OH2:6].O.O.[Na+].[Br:10][C:11]1[CH:17]=[C:16]([F:18])[C:14]([NH2:15])=[C:13]([F:19])[CH:12]=1>C(O)(=O)C>[Br:10][C:11]1[CH:17]=[C:16]([F:18])[C:14]([N+:15]([O-:6])=[O:5])=[C:13]([F:19])[CH:12]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 mL), stirred at 55° C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55° C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5×100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the title compound as a tan solid. 1H NMR (CDCl3) δ 7.32 (dt, 2H).
Workup
- stirringAfter stirring at 55° C. for an additional 3 hours
- temperatureto cool to room temperature
- filtrationfiltered
- additionThe filtrate was poured into ice
- extractionextracted twice with ethyl acetate
- washThe combined organic extracts were washed successively with 5×100-mL portions of water, brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography over silica gel
- washeluted with ethyl acetate:hexanes (1:20)
Sources & evidence
- ORD record
- ord-81d53362667a4521a8de5627791b8689
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188095B2
Reaction notes
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