3-Methylpyridine → 3-(12-Bromododecyl)-pyridine
Reaction equation
[Li+].CC([N-]C(C)C)C.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.[NH4+].[Cl-]>C1COCC1>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][Br:16])[CH:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
LDA (2 M) (10.5 mL, 21.22 mmol) was added drop-wise to a solution of 3-picoline (2.17 g, 23.34 mmol) in THF (60 mL) at −78° C. The mixture was stirred for 30 min and then 1,11-dibromoundecane (10 g, 31.83 mmol) was added in one portion. The resulting mixture was warmed to 0° C. and stirred for 4 hrs. Fifty percent saturated NH4Cl was added to the reaction mixture. The aqueous phase was extracted with ethylacetate (2×40 mL), and the combined organic liquors were washed with 50% saturated brine (3×40 mL) and saturated brine (40 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (hexanes:ethylacetate 4:1) to afford 4.47 g 12-(pyridin-3-yl)-1-bromododecane. Yield: 59%.
Workup
- stirringstirred for 4 hrs
- extractionThe aqueous phase was extracted with ethylacetate (2×40 mL)
- washthe combined organic liquors were washed with 50% saturated brine (3×40 mL) and saturated brine (40 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography (hexanes:ethylacetate 4:1)
Sources & evidence
- ORD record
- ord-36a08a3a1b144bb2bb4c1f843d27409c
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653275B2
Reaction notes
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