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3-bromo-4-vinylpyridine synthesis

3synthesis methods
75927-49-0 Synthesis
Pinacol vinylboronate

75927-49-0
206 suppliers
$6.00/1g

3-bromo-4-vinylpyridine

1255957-49-3
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Yield:1255957-49-3 92%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium phosphate in water;N,N-dimethyl-formamide at 60;Inert atmosphere;

Steps:



A mixture of compound 1 (237 mg, 1 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (154 mg, 1 mmol), aq. K3PO4 (3 mL, 1 M, 3 mmol) and Pd(dppf)Cl2 (73 mg, 0.1 mmol) in DMF (10 mL) was stirred at 60 °C under N2 for 3 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by silica gel column chromatography (PE : EA = 30:1) to give the product of compound 2 (170 mg, yield: 92 %). 1H-NMR (CDCl3, 400 MHz) d 8.70 (s, 1H), 8.45 (d, J = 7.2Hz, 1H), 7.41 (d, J = 7.2Hz, 1H), 6.98 (q, J = 6.8Hz, 1H), 5.94 (d, J = 17.6Hz, 1H), 5.60 (d, J = 11.2Hz, 1H).

References:

He, Shuwen;Li, Peng;Dai, Xing;Liu, Hong;Lai, Zhong;Xiao, Dong;McComas, Casey C.;Du, Chunyan;Liu, Yuehui;Yin, Jingjun;Dang, Qun;Zorn, Nicolas;Peng, Xuanjia;Nargund, Ravi P.;Palani, Anandan [Tetrahedron Letters,2017,vol. 58,# 14,p. 1373 - 1375] Location in patent:supporting information