Tetrabutylammonium Fluoride → HCID 86686336, compound

HRID 1043903Notes

Reaction equation

HRID 1043903 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[N:4][C:5]([CH2:9]Br)=[CH:6][C:7]=1[CH3:8].CCCC[N+](CCCC)(CCCC)CCCC.[F-:29]>>[Br:1][C:2]1[C:3]([CH3:11])=[N:4][C:5]([CH2:9][F:29])=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86686334HCID 86686334, compound

Product 1

HCID 86686336HCID 86686336, compound

Procedure

A mixture of 3-bromo-6-(bromomethyl)-2,4-dimethylpyridine obtained in Preparation Example 30(1) (2.00 g) and TBAF (35.8 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 50%) to give the title compound (572 mg). 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.44 (s, 3H), 2.67 (s, 3H), 5.28-5.47 (m, 2H), 7.14-7.19 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 50%)

Sources & evidence

ORD record
ord-8e36c612f2fd4719beabd882c948fd52
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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