Tetrabutylammonium Fluoride → HCID 86686338, compound

Reaction equation

[Br:1][C:2]1[C:3]([CH2:10]Br)=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].CCCC[N+](CCCC)(CCCC)CCCC.[F-:29]>>[Br:1][C:2]1[C:3]([CH2:10][F:29])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 86686337HCID 86686337, compound

Product 1

HCID 86686338HCID 86686338, compound

Procedure

A mixture of 3-bromo-2-(bromomethyl)-4,6-dimethylpyridine (1.00 g) and TBAF (17.9 mL, 1 M solution in THF) was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 30%) to give the title compound (651 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 30%)

Sources & evidence

ORD record: ord-641ade8db95e44018bf6e263c49f7f37
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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