Benzoic acid, 4-amino-3-nitro- → 4-Amino-3-bromo-5-nitrobenzoic acid
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Br:14]NC(=O)CCC(N)=O>ClCCl.CN(C)C=O>[NH2:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]=1[Br:14]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-amino-3-nitrobenzoic acid (2.50 g, 13.7 mmol) in dichloromethane (65.4 mL) and N,N-dimethylformamide (3.3 mL) was added N-bromosuccinamide (2.69 g, 15.1 mmol). The mixture was stirred at ambient temperature. After 15 min, the mixture was quenched with saturated sodium sulfite. Hydrochloric acid (1.0 M) was added and the mixture was extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated (3.65 g). LC-MS [M]=261.0.