Tetrabutylammonium Fluoride → 3-Bromo-2-(fluoromethyl)-6-methoxy-4-methylpyridine
Reaction equation
[Br:1][C:2]1[C:3]([CH2:11]Br)=[N:4][C:5]([O:9][CH3:10])=[CH:6][C:7]=1[CH3:8].CCCC[N+](CCCC)(CCCC)CCCC.[F-:30]>>[Br:1][C:2]1[C:3]([CH2:11][F:30])=[N:4][C:5]([O:9][CH3:10])=[CH:6][C:7]=1[CH3:8]Participants
3
Procedure
A mixture of 3-bromo-2-(bromomethyl)-6-methoxy-4-methylpyridine (126 mg) and TBAF (1.71 mL, 1 M solution in THF) was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (37 mg).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)
Sources & evidence
- ORD record
- ord-6be50967bf7f4a1a9d22e9f549658854
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563565B2
Reaction notes
Loading…