ChemicalBook CAS DataBase List 5-BROMO-2,2'-BIPYRIDINE

5-BROMO-2,2'-BIPYRIDINE synthesis

12synthesis methods

Product Name:5-BROMO-2,2'-BIPYRIDINE
CAS Number:15862-19-8
Molecular formula:C10H7BrN2
Molecular Weight:235.08

624-28-2

13737-05-8

15862-19-8

The general procedure for the synthesis of 5-bromo-2,2'-bipyridine from 2,5-dibromopyridine and 2-(trimethylstannyl)pyridine was as follows: 1.91 g (7.89 mmol, 1.0 eq.) of 2-(trimethylstannyl)pyridine and 2.08 g (8.77 mmol, 1.1 eq.) of 2,5-dibromopyridine were dissolved in 16 mL of freshly distilled xylene. The solution was degassed and 0.061 g (0.053 mmol, 0.06 eq.) of Pd(PPh3)4 was added and stirred under reflux conditions for 15 hours. Upon completion of the reaction, 40 mL of 2N NaOH solution was added, followed by three extractions with 40 mL of toluene. The organic phases were combined, washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to remove the solvent. Purification by silica gel column chromatography (SiO2, 3.3 × 10 cm, pentane/EtOAc = 20:1) afforded 2.57 g (63% yield) of 5-bromo-2,2'-bipyridine as a colorless solid.

624-28-2 Synthesis

624-28-2
722 suppliers
$5.00/5g

13737-05-8
36 suppliers
$155.00/1g

15862-19-8
152 suppliers
$20.00/100mg

Yield:15862-19-8 63%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 5,5-dimethyl-1,3-cyclohexadiene; for 15 h;Reflux;

Steps:

5-Bromo-2,2’-bipyridine

1.91 g (7.89 mmol, 1.0 eq) 2-(trimethylstannyl)pyridine and 2.08 g (8.77 mmol, 1.1 eq), 2,5-dibromopyridine are dissolved in 16 mL freshly distilled xylene. The degassed solution is treated with0.061 g (0.053 mmol, 0.06 eq) Pd(PPh3)4 and stirred under reflux for 15 hours. After addition of 40 mL2N NaOH, the mixture is extracted with 40 mL toluene (3x). The organic phase is washed with brine,dried over MgSO4 and the solvent is removed in vacuo. Purification via column chromatography (SiO2,3.5 x 10 cm, pentane/EtOAc = 20/1 10/1) yields 2.57 g (63%) 5-bromo-2,2’-bipyridine as colourlesssolid.

References:

B?hm, Alexander;Bach, Thorsten [Synlett,2016,vol. 27,# 7,p. 1056 - 1060] Location in patent:supporting information

624-28-2 Synthesis

624-28-2
722 suppliers
$5.00/5g