Trimethylamine oxide → Methyl 2-bromo-3-methoxypropanoate

Methyl 2,3-dibromopropionate (21.9 g) and trimethylamine N-oxide (0.1 g) in methanol (8 ml) were cooled to −5° C. with stirring under an atmosphere of nitrogen. A solution of sodium methoxide [freshly prepared from sodium (2.25 g) and methanol (24 ml)] was added dropwise over 15 minutes to the mixture, which was maintained below 0° C. by cooling. On completion of the addition, the mixture was stirred for a further 30 minutes and acetic acid (1 ml) was added followed by diethyl ether (100 ml). The mixture was filtered to remove insoluble salts and the filtrate evaporated under reduced pressure to give an oil, which was re-dissolved in a small volume of diethyl ether and re-filtered. The filtrate was evaporated under reduced pressure to give the required product, 17.4 g, as a pale yellow oil.

1. additionwas added dropwise over 15 minutes to the mixture, which
2. temperaturewas maintained below 0° C.
3. temperatureby cooling
4. additionOn completion of the addition
5. stirringthe mixture was stirred for a further 30 minutes
6. filtrationThe mixture was filtered
7. customto remove insoluble salts
8. customthe filtrate evaporated under reduced pressure
9. customto give an oil, which
10. filtrationre-filtered
11. customThe filtrate was evaporated under reduced pressure

ORD record

ord-dc227326b8e341908f0574b2b808f7fc

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166621B2