2-Amino-5-chlorobenzoic acid → 2-Amino-3-bromo-5-chlorobenzoic acid
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br>CC(O)=O>[NH2:1][C:2]1[C:10]([Br:12])=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
To a solution of 200 g (1.05 mol) of 2-amino-5-chlorobenzoic acid in 3.4 L of HOAc at 15° C. was added dropwise 184 g (1.15 mol) of Br2. The mixture was stirred at 15° C. for 4 hrs, quenched slowly into 8 L of water, and extracted with 2×2 L of t-BuOMe. The combined extract was washed with water, dried over MgSO4 and concentrated. The crude product was treated with hot hexane, filtered and dried to give 210 g (80%) of 2-amino-3-bromo-5-chlorobenzoic acid as white solid. Mp. 225-2280° C. 1H NMR (DMSO-d6): δ7.70 (d, J=2.6 Hz, 1 H), 7.69 (d, J=2.6 Hz, 1 H), 6.8 (bs, 2 H). 13C NMR (DMSO-d6): δ168.16, 147.06, 136.25, 130.19, 118.22, 112.35,110.34. IR:3480 (m), 3350 (m), 2920 (s), 1670 (s) cm-1. Analysis calcd. for C7H5BrClNO2 : C, 33.53, H, 2.00, N, 5.59; Found: C, 33.63, H, 2.12, N, 5.70. ##STR22##