Water → HCID 21196241, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[CH3:13][NH:14][CH3:15].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([N:14]([CH3:15])[CH3:13])=[O:8]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Bromo-2-fluorobenzoic acid (500 mg, 2.23 mmol) was dissolved in DMF (5.0 mL), and dimethylamine hydrochloride (223 mg, 2.72 mmol), WSC.HCl (511 mg, 2.66 mmol), HOBt.H2O (410 mg, 2.68 mmol), and potassium carbonate (367 mg, 2.66 mmol) were added thereto, and the mixture was stirred at room temperature for 3 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50) to give 5-bromo-2-fluoro-N,N-dimethylbenzamide (550 mg, 2.23 mmol, yield: 99%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50)
Sources & evidence
- ORD record
- ord-74a7fc93c782410baffad9292a6319d6
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273738B2
Reaction notes
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