Methanol → Methyl 2-bromo-3-methoxypropanoate

480 g of mercuric acetate was added to a solution of 139 g of methyl acrylate in 170 ml of methanol. The resulting mixture was stirred for 3 days at room temperature. To the mixture, cooled by an ice bath, a solution of 100 g of potassium bromide in 600 ml of water was added. A heavy oil formed, was separated from the mixture and was extracted with chloroform. The extract was washed with water, dried (MgSO4) and filtered. The filtrate was heated to 60° C. and 36.9 g of bromine was added, drop-by-drop over a 2-hour period. The resulting mixture was cooled to 5° C. and concentrated in a rotary evaporator. The liquid residue was distilled to give methyl 2-bromo-3-methoxypropionate (10A), b.p.: 69°-72° C. (3-5 Torr.).

1. temperatureTo the mixture, cooled by an ice bath
2. customA heavy oil formed
3. customwas separated from the mixture
4. extractionwas extracted with chloroform
5. washThe extract was washed with water
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. temperatureThe filtrate was heated to 60° C.
9. addition36.9 g of bromine was added, drop-by-drop over a 2-hour period
10. temperatureThe resulting mixture was cooled to 5° C.
11. concentrationconcentrated in a rotary evaporator
12. distillationThe liquid residue was distilled

ORD record

ord-4f6fb750c81b4cbba340e968d82d1e0a

Source dataset

uspto-grants-1984_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04439226