ChemicalBook CAS DataBase List 2-Bromo-6-phenylpyridine

2-Bromo-6-phenylpyridine synthesis

13synthesis methods

Product Name:2-Bromo-6-phenylpyridine
CAS Number:39774-26-0
Molecular formula:C11H8BrN
Molecular Weight:234.09

626-05-1

98-80-6

39774-26-0

General procedure for the synthesis of 2-bromo-6-phenylpyridine from 2,6-dibromopyridine and phenylboronic acid: 2,6-dibromopyridine (2 g, 8.44 mmol), phenylboronic acid (1.03 g, 8.44 mmol), potassium carbonate (4.67 g, 33.77 mmol), and tetrabutylammonium bromide (TBAB, 271 mg, 0.84 mmol) were mixed in a 1 ,4-dioxane (16 ml) and water (4 ml) in a solvent mixture. The reaction mixture was degassed by blowing in nitrogen for 30 min, followed by addition of dichlorobis(triphenylphosphine)palladium(II) (PdCl2(dppf), 62 mg, 0.084 mmol). The reaction mixture was stirred at 40 °C for 1 h. After completion of the reaction, the reaction was filtered through diatomaceous earth. The filtrate was collected and the solvent was removed by distillation under reduced pressure. The crude product was purified by column chromatography using 100% petroleum ether as eluent to afford the target compound 2-bromo-6-phenylpyridine as a colorless solid (1.85 g, 93% yield).1H NMR (400 MHz, DMSO) δ 8.56 (dd, J = 6.3,2.4 Hz, 1H), 8.36-8.18 (m, 2H). 8.16-8.00 (m, 2H), 7.61-7.53 (m, 2H), 7.53-7.45 (m, 1H).

626-05-1 Synthesis

626-05-1
512 suppliers
$9.00/10g

98-80-6 Synthesis

98-80-6
745 suppliers
$5.00/5g

39774-26-0
117 suppliers
$41.00/250mg

3558-69-8
114 suppliers
$68.00/5g

Yield: 80%

Reaction Conditions:

with (+/-)-7-(2,3-diacetoxypropyl)theophylline;palladium diacetate;lithium carbonate in water at 120; for 0.166667 h;Microwave irradiation;Green chemistry;Suzuki-Miyaura Coupling;

Steps:

Suzuki-Miyaura couplings were performed in glass tubes suitable for
General procedure: Suzuki-Miyaura couplings were performed in glass tubes suitable for microwave. Halopyridines (0.44 mmol), phenyl boronic acid (65.17 mg, 0.53 mmol), Li₂CO₃(63.7 mg, 0.89 mmol), 1 mol % of Pd(OAc)₂(1 mg, 4.45 ϰ 10^-3 mol), and 2 mol % of the corresponding ligand in 3 mL of distilled water. The mixtures were stirred and heated at 120 °C under microwave radiation during 10 min with a ramp of 1 min in a CEM Discover reactor coupled to a CEM Explorer robotic system. The resulting reaction mixture was cooled to room temperature and the mixture extracted with CH₂Cl₂ (3 ϰ 2 mL), the organic phase was treated with anhydrous Na₂SO₄ after filter over celite and analyzed by Gas Chromatography (GC-MS) on an Agilent 6890N GC with a 30.0 m DB-1MS capillary column coupled to an Agilent 5973 Inert Mass Selective detector. Additional experiments of catalysis were carried out under the same reaction conditions using different bases Na₂CO₃, K₂CO₃, Li₂CO₃, Cs₂CO₃, Rb₂CO₃, NaOH, KOH, Et₃N, and DIPEA.