ChemicalBook CAS DataBase List 3-BroMo-5-(prop-1-en-2-yl)pyridine

3-BroMo-5-(prop-1-en-2-yl)pyridine synthesis

7synthesis methods

Product Name:3-BroMo-5-(prop-1-en-2-yl)pyridine
CAS Number:40472-88-6
Molecular formula:C8H10BrNO
Molecular Weight:216.08

20986-40-7 Synthesis

20986-40-7
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$6.00/10g

75-16-1
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$12.00/10ml

40472-88-6
62 suppliers
$45.00/10mg

Yield: 92%

Reaction Conditions:

Stage #1:ethyl 5-bromo-3-pyridinecarboxylate;methylmagnesium bromide in tetrahydrofuran;diethyl ether at 30;
Stage #2: with water;ammonium chloride in tetrahydrofuran;diethyl etherCooling with ice;

Steps:

3.1
Add a solution of ethyl 5-bromopyridine-3-carboxylate (22.5 g, 98 mmol) in tetrahydrofuran (350 m L) to a solution of 3M methylmagnesium bromide in diethyl ether (98 mL, 293 mmol, 3 eq.) with internal temperature below 30'C. Upon completion of reaction, cool the mixture in an ice bath and quench with saturated aqueous ammonium chloride and keep stirring until most solids dissolve. Add water (500 mL) and extract with ethyl acetate (3×500 mL). Dry the organic layer over sodium sulfate, filter and concentrate the organic layer to a residue. Purify the residue by silica gel column chromatography eluting with solvent of ethyl acetate:hexane (1:1), to afford the titled product as an oil (19.4 g, 92%). MS (ESI) m/z (M+H)⁺214.9, 216.9.

References:

ELI LILLY AND COMPANY US2012/184577, 2012, A1 Location in patent:Page/Page column 3

29681-44-5 Synthesis