Ethyl Acrylate → Ethyl 3-(m-bromophenoxy)propionate

A solution of 3-bromophenol (10.0 g, 57.8 mmole) in 50 mL of ethyl acrylate was treated with 0.9 mL of Triton B. The reaction mixture was heated at reflux for 18 hours. Excess ethyl acrylate was removed by distillation at atmospheric pressure. The resulting residue was diluted with 50 mL toluene and co-evaporated. The remaining product was diluted in 100 mL ether and washed with two 50 mL portions of sodium carbonate solution, 50 mL water and 50 mL saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow liquid. The product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes) to afford 6.435 g of 3-(3-bromo-phenoxy)-propionic acid ethyl ester as a colorless liquid.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 18 hours
3. customExcess ethyl acrylate was removed by distillation at atmospheric pressure
4. additionThe resulting residue was diluted with 50 mL toluene
5. additionThe remaining product was diluted in 100 mL ether
6. washwashed with two 50 mL portions of sodium carbonate solution, 50 mL water and 50 mL saturated aqueous sodium chloride solution
7. dry with materialThe organic phase was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a pale yellow liquid
11. customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes)

ORD record

ord-3cc2ce2e54fa4dccab57d92f471e7d55

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354931B2