2,6-Dibromopyridine → 2-Bromo-6-(hex-1-yn-1-yl)pyridine

HRID 1197187Notes

Reaction equation

HRID 1197187 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(N(CC)CC)C>[Br:8][C:4]1[N:3]=[C:2]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 122742,6-DibromopyridineHCID 127321-Hexyne

Product 1

HCID 198974002-Bromo-6-(hex-1-yn-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

2,6-Dibromopyridine (2.36 g, 10 mmole) is suspended in 32 ml degassed triethylamine in a 100 ml one-neck round bottom flask under argon. The suspension is treated successively with (bis)triphenylphosphine palladium dichloride (62 mg, 0.08 mmole) and cuprous iodide (8 mg, 0.04 mmole) and is warmed to 50° C. 1-Hexyne (0.50 ml, 4.4 mmole), in 4 ml triethylamine, is added slowly dropwise to the reaction mixture over 30 minutes at 50° C. The reaction is stirred an additional one hour at 50° C., cooled to room temperature, and the triethylamine hydrobromide is removed by filtration. The filtrate is concentrated in vacuo to a white pasty solid.

Workup

  1. customdegassed triethylamine in a 100 ml one-neck round bottom flask under argon
  2. temperaturecooled to room temperature
  3. customthe triethylamine hydrobromide is removed by filtration
  4. concentrationThe filtrate is concentrated in vacuo to a white pasty solid

Sources & evidence

ORD record
ord-31758fc3336640e89312dc7e12f4cca8
Source dataset
uspto-grants-1992_05
Patent number
US05116981

Reaction notes

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