ChemicalBook CAS DataBase List 3-BROMO-2-PHENYLPYRIDINE

3-BROMO-2-PHENYLPYRIDINE synthesis

4synthesis methods

Product Name:3-BROMO-2-PHENYLPYRIDINE
CAS Number:91182-50-2
Molecular formula:C11H8BrN
Molecular Weight:234.09

13534-89-9

98-80-6

91182-50-2

General procedure for the synthesis of 3-bromo-2-phenylpyridine from 2,3-dibromopyridine and phenylboronic acid: a screw-capped vial was charged with a solvent mixture of acetonitrile (MeCN) and methanol (MeOH) (2:1, 15 mL), 2,3-dibromopyridine (474 mg, 2.0 mmol), phenylboronic acid (2.1 mmol), potassium carbonate (K2CO3, 560 mg, 4.0 mmol), triphenylphosphine (PPh3, 52 mg, 10 mol%) and palladium acetate (Pd(OAc)). 4.0 mmol), triphenylphosphine (PPh3, 52 mg, 10 mol%) and palladium acetate (Pd(OAc)2, 23 mg, 5 mol%). The reaction mixture was displaced three times with argon to remove oxygen, sealed and placed in a 50°C oil bath with stirring for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad to remove solid impurities. The filtrate was concentrated under reduced pressure and the resulting residue was dissolved in dichloromethane (CH2Cl2, 20 mL) and subsequently washed with water (3 x 10 mL) and the organic phase was dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel column chromatography with the eluent being petroleum ether-ethyl acetate (30:1) to afford pure 3-bromo-2-phenylpyridine (2a) in the yield of 387 mg (83%) as a colorless oil.

13534-89-9
327 suppliers
$6.00/1g

98-80-6 Synthesis

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

91182-50-2
82 suppliers
$55.00/50mg

Yield:91182-50-2 95%

Reaction Conditions:

with palladium diacetate;potassium carbonate;triphenylphosphine in methanol;acetonitrile at 50; for 24 h;Inert atmosphere;regioselective reaction;Suzuki Coupling;

Steps:

Typical procedure for the 2-arylation of 2,5- and 2,3-dibromopyridines

General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K₂CO₃ (0.14 g, 1.0 mmol), Pd(OAc)₂ (11 mg, 5 mol %), PPh₃ (26 mg, 10 mol %) were dissolved in CH₃CN/CH₃OH (2:1, 6 mL). The solution was stirred at 50 °C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH₂Cl₂ (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid.

References:

Zhou, Qizhong;Zhang, Bin;Su, Liangjun;Jiang, Tiansheng;Chen, Rener;Du, Tieqi;Ye, Yuyuan;Shen, Jianfen;Dai, Guoliang;Han, Deman;Jiang, Huajiang [Tetrahedron,2013,vol. 69,# 51,p. 10996 - 11003]

626-55-1 Synthesis