Chlorosuccinimide → 4-Chloro-2,3-difluoro-6-nitroaniline
Reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[Cl:13][C:7]1[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[F:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
2,3-Difluoro-6-nitroaniline (15.4 g, 88.7 mmol), N-chlorosuccinimide (14.9 g, 111.4 mmol) and N,N-dimethylformamide (250 mL) were combined and were heated to 80-90° C. for several hours, after which time the mixture was poured into ice water. The product was extracted with ethyl acetate which was then washed with water, saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and the solvents were removed in vacuo to leave a yellow, viscous oil. 1H NMR (DMSO-d6) δ: 8.03 (dd, J=7.3, 2.2 Hz, 1H, Ar—H), 7.65 (br s, 2H, NH2).