Water → 4-Bromo-2-fluoro-6-(trifluoromethyl)aniline
Reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[Br:13]N1C(=O)CCC1=O.O>C(#N)C.[Fe](Cl)(Cl)Cl>[Br:13][C:5]1[CH:4]=[C:3]([C:9]([F:12])([F:10])[F:11])[C:2]([NH2:1])=[C:7]([F:8])[CH:6]=1Participants
6
Procedure
To a solution of 2-amino-3-fluorobenzotrifluoride (0.7 ml, 5.6 mmol) in acetonitrile (2 ml) was added N-bromosuccinimide (994 mg, 5.6 mmol), followed by iron (III) chloride (90.1 mg, 0.6 mmol). The reaction mixture was stirred at room temperature for 90 min, before addition of water (20 ml). The mixture was extracted with tert-butyl methyl ether (2×15 ml) and the combined extracts were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo to give the title compound (1.4 g), which was used directly.
Workup
- extractionThe mixture was extracted with tert-butyl methyl ether (2×15 ml)
- washthe combined extracts were washed with brine (20 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-20fbcb420ed74f65a231273ccce2ce69
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608604B2
Reaction notes
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