Bromine → ETHYL 3-(6,7-DIBROMO-2,3-DIHYDRO-1-BENZOFURAN-5-YL)PROPANOATE

Bromine (0.80 g, 5.01 mmol) was added dropwise to a mixture of ethyl 3-(7-bromo-2,3-dihydrobenzofuran-5-yl)propionate (1.0 g, 3.34 mmol) and iron (10 mg) in acetic acid (10 ml) and the reaction mixture was stirred at 50° C. for 5 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Water was added to the residue and the organic matter was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give 0.67 g (yield: 53%) of the target compound.

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionWater was added to the residue
4. extractionthe organic matter was extracted with ethyl acetate
5. washThe extract was washed with a saturated aqueous sodium bicarbonate solution
6. dry with materiala saturated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

ORD record

ord-953efe86fe454e2b81e564616619a03e

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06034239