Water → 2-Bromo-4-fluoro-6-nitroaniline
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:12][C:7]1[C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=[C:2]([F:1])[CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Bromo-4-fluoro-2-nitroaniline was prepared using an adaptation of the method of Mitchell et al., J. Org. Chem. 44: 4733 (1979). To a solution of 4-fluoro-2-nitroaniline (500 mg, 3.2 mmol) in dry DMF (16 mL) under N2 was added dropwise a solution of N-bromosuccinimide (570 mg, 3.2 mmol) in dry DMF (16 mL). The reaction was allowed to stir 24 h. The solution was then poured into 100 mL H2O and this aqueous phase extracted with 4×25 mL CH2Cl2. The combined organic phases were washed with 3×4 mL H2O and dried (MgSO4). The MgSO4 was vacuum filtered and the solvent rotary evaporated to yield a brown oil which crystallized on standing. 642 mg (85.4%). 1H NMR (CDCl3) δ 6.51 (br s, 2H NH2), 7.58 (dd, JH4-3 -3 Hz, JH4-F =6.5 Hz, H-4), 7.92 (dd, JH3-F =3 Hz, JH3-F =8.7 Hz, H-3).