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

HRID 1636588Notes

Reaction equation

[Br:1]Br.[Br:3][C:4]1[C:12]2[O:11][CH2:10][CH2:9][C:8]=2[CH:7]=[C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=1>C(O)(=O)C.[Fe]>[Br:1][C:5]1[C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:8]2[CH2:9][CH2:10][O:11][C:12]=2[C:4]=1[Br:3]

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-953efe86fe454e2b81e564616619a03e
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034239

Reaction notes

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