Methyl 2-(broMoMethyl)nicotinate synthesis
- Product Name:Methyl 2-(broMoMethyl)nicotinate
- CAS Number:116986-08-4
- Molecular formula:C8H8BrNO2
- Molecular Weight:230.06
65719-09-7
116986-08-4
General procedure for the synthesis of methyl 2-(bromomethyl)nicotinate from methyl 2-methylnicotinate: methyl 2-methylnicotinate (4.1 g, 27.1 mmol), N-bromosuccinimide (NBS, 5.8 g, 32.5 mmol) and azobisisobutyronitrile (AIBN, 100 mg, 0.61 mmol) were dissolved in carbon tetrachloride (55 mL). The reaction mixture was stirred at 90 °C for 16 h under nitrogen protection. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with water (25 mL), followed by extraction of the aqueous layer with dichloromethane (50 mL x 3). The organic layers were combined and concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by silica gel column chromatography to afford the target product methyl 2-(bromomethyl)nicotinate (5.0 g, 80.6% yield). The product was analyzed by LCMS, m/z: 229.9 ([M+H]+).
65719-09-7
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$21.00/1g
116986-08-4
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$45.00/10mg
Yield: 80.6%
Reaction Conditions:
with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 90; for 16 h;Inert atmosphere;
Steps:
10.2 methyl 2-(bromomethyl)nicotinate
A mixture of methyl 2-methylnicotinate (4.1 g, 27.1 mmol), NBS (5.8 g, 32.5 mmol), AIBN (100 mg, 0.61 mmol) in carbon tetrachloride (55 mL) was stirred at 90 °C for 16 h under nitrogen. Once cooled, the reaction mixture was diluted with water (25 mL) and the aqueous layer was extracted with dichloromethane (50 mL x 3). The combined organic layers were concentrated in vacuo, and the resulting residue was purified by flash chromatography on Si02 to give the desired product (5.0 g, 80.6%). LCMS (mlz): 229.9 (M+ 1).
References:
EPIZYME, INC.;DUNCAN, Kenneth, W.;CHESWORTH, Richard;MUNCHHOF, Michael, John;SHAPIRO, Gideon WO2015/200677, 2015, A2 Location in patent:Paragraph 00522; 00523
38749-79-0
381 suppliers
$8.00/1g
116986-08-4
60 suppliers
$45.00/10mg