Dimethylformamide → Methyl 2-bromo-5-ethoxy-2'-fluorobiphenyl-4-carboxylate
Reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH:18]=[CH:19][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:13].CN(C=O)C>O>[Br:1][C:18]1[CH:19]=[C:20]([C:21]([O:23][CH3:24])=[O:22])[C:15]([O:14][CH2:12][CH3:13])=[CH:16][C:17]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31]Participants
5
Procedure
Dibromoisocyanuric acid (0.631 g) was added to a mixture of methyl 3-ethoxy-2′-fluorobiphenyl-4-carboxylate (1.14 g) and DMF (10 mL), and the resultant mixture was stirred at room temperature for 2 hours. Dibromoisocyanuric acid (0.238 g) was further added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.39 g).
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe obtained organic layer was washed with water and saturated saline
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-6078728b663248d0adbac8d57440be09
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353108B2
Reaction notes
Loading…