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-dichlorobenzoic 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 in vaccuo and the residue was partitioned between water (200 mL) and ethyl acetate (200 mL). The organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2×100 mL). The combined organics were dried over anhydrous sodium sulfate and concentrated to afford 3-amino-4-bromo-2,6-dichloro-benzoic acid (5 g, 73%).
Workup
- customAcetonitrile was removed in vaccuo
- customthe residue was partitioned between water (200 mL) and ethyl acetate (200 mL)
- customThe organic layer was separated
- extractionthe aqueous layer was again extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined organics were dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6d591217143646f0b31c819ba6b74714
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09364466B2
Reaction notes
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