Methyl-3-bromopropiolate synthesis
- Product Name:Methyl-3-bromopropiolate
- CAS Number:23680-40-2
- Molecular formula:C4H3BrO2
- Molecular Weight:162.97
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Yield: 88%
Reaction Conditions:
with silver nitrate in acetone at 20; for 6 h;
Steps:
Preparation of tert-butyl (1S,2R,4R)-2-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate
Methyl propiolate (52 ml, 0.583 mol) is combined with recrystallized N- bromo-succinimide (120 g, 0.674 mol) in 1,700 ml acetone under nitrogen. The solution is treated with silver nitrate (9.9 g, 0.0583 mol) neat in a single lot and the reaction is stirred 6 h at RT. The acetone is removed under reduced pressure (25C, bath temperature) to provide a gray slurry. The slurry is washed with 2 x 200 ml hexane, the gray solid is removed by filtration, and the filtrate is concentrated in vacuo to provide 95 g of a pale yellow oily residue. The crude material is distilled via short path under reduced pressure (65C, about 25 mm Hg) into a dry ICE/ACETONE cooled receiver to give 83.7 g (88%) of methyl-3-bromo-propiolate as a pale yellow oil. Anal. calc'd for C4H3BRO2 : C, 29.48 ; H, 1.86. Found: C, 29.09 ; H, 1.97.
References:
PHARMACIA & UPJOHN COMPANY WO2004/39815, 2004, A2 Location in patent:Page 44
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23680-40-2
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23680-40-2
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