2,6-Lutidine → 2-Bromo-1-(6-methylpyridin-3-yl)ethanone
Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:31]N1C(=O)CCC1=O>O.C(Cl)(Cl)Cl>[Br:31][CH2:9][C:8]([C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]Participants
Procedure
To a chloroform (6.5 mL) solution of 1-(6-methylpyridin-3-yl)ethanone (0.43 g), under ice cooling in a nitrogen atmosphere, 2,6-lutidine (0.63 mL) and trimethylsilyl trifluoromethanesulfonate (0.69 mL) were added, and the resultant was stirred for 30 minutes. Then, N-bromosuccinimide (0.63 g) was added thereto, and the resultant was stirred at room temperature for 1 hour. Water was added to the reaction solution, and the resultant was stirred for 15 minutes, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→70/30) to obtain the title compound (0.24 g) as a light brown solid.
Workup
- stirringthe resultant was stirred at room temperature for 1 hour
- stirringthe resultant was stirred for 15 minutes
- extractionfollowed by extraction with chloroform
- customAn organic layer was separated
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→70/30)
Sources & evidence
- ORD record
- ord-b98720bd497148e89e2831b1d2979126
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045466B2
Reaction notes
Loading…