Pyridine → 3-(3-bromo-4-fluoro-phenyl)-N-methoxy-N-methylacrylamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11](Cl)=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].Cl.[CH3:15][NH:16][O:17][CH3:18].N1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([N:16]([O:17][CH3:18])[CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]Participants
Procedure
The unpurified 3-(3-bromo-4-fluoro-phenyl)-acryloyl chloride (3.5 g, 13.3 mmol) prepared in Step 2, N,O-dimethylhydroxylamine hydrochloride (1.4 g, 14.0 mmol), and pyridine (2.4 mL, 29.4 mmol) were added at 0° C. to dichloromethane (20.0 mL). The reaction mixture was stirred at room temperature for 12 hours, quenched with a 1N hydrochloric acid solution, and then extracted with diethyl ether two times. The combined extract was washed with a saturated solution of sodium hydrogen carbonate and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was recrystallized from diethyl ether and n-hexane to give 3.2 g of the titled compound as a white solid.
Workup
- customquenched with a 1N hydrochloric acid solution
- extractionextracted with diethyl ether two times
- extractionThe combined extract
- washwas washed with a saturated solution of sodium hydrogen carbonate and brine
- dry with materialdried on anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto give a yellow liquid residue
- customThe resulting residue was recrystallized from diethyl ether and n-hexane
Sources & evidence
- ORD record
- ord-66949d7b1ebd4b75bae9aae74855d040
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376420B2
Reaction notes
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