N-bromobutanimide → 3-Amino-4-bromo-2,6-dichlorobenzoic acid
Reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([C:8]([Cl:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Br:13]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([C:8]([Cl:11])=[CH:9][C:10]=1[Br:13])[C:5]([OH:7])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 3-amino-2,6-dichloro-benzoic acid (5 g, 24 mmol, Step b) in acetonitrile (50 mL) was treated with N-bromosuccinimide (5.1 g, 29 mmol) and the reaction mixture was stirred at 90° C. for 45 minutes. Acetonitrile was removed under vacuum and the residue was partitioned between water (200 mL) and ethyl acetate (200 mL). Organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2×100 mL). The combined organic layer was dried over anhydrous sodium sulphate and concentrated to yield 3-amino-4-bromo-2,6-dichloro-benzoic acid (5 g, 73%).
Workup
- customAcetonitrile was removed under vacuum
- customthe residue was partitioned between water (200 mL) and ethyl acetate (200 mL)
- customOrganic layer was separated
- extractionthe aqueous layer was again extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2ff9645daf2d40f69893aa5e0f929871
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09364466B2
Reaction notes
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