Bromine → 2-Bromo-6-fluoro-4-nitrotoluene
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:12]Br>[Fe]>[Br:12][C:6]1[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=[C:2]([F:1])[C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To 3-fluoro-4-methylnitrobenzene (4.0 gm, 25.8 mmol) was added bromine (5.2 gm, 32 mmol) and iron powder (100 mg). The mixture was heated under a condenser at 100° C. for 40 hr and then poured into ice water containing enough sodium sulfite to quench the excess bromine. The aqueous layer was extracted twice with ether and the ether layers were washed with brine, dried over sodium sulfate, combined and evaporated. The residue was purified by FC (10-20% ethyl acetate/hexanes) to afford 1.4 gm of the title compound as a white solid (the major and highest Rf isomer). NMR (CDCl3): δ 2.41 (d, 3H, J=3 Hz), 7.85 (dd, 1H, J=2.1 and 9 Hz), 8.24 (dd, 1H, J=1.8 and 2.1 Hz).
Workup
- customto quench the excess bromine
- extractionThe aqueous layer was extracted twice with ether
- washthe ether layers were washed with brine
- dry with materialdried over sodium sulfate
- customevaporated
- customThe residue was purified by FC (10-20% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-a24ccd3afe1d4fa38495de182ef3a319
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877191
Reaction notes
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