Water → HCID 21193678, compound

HRID 1067466Notes

Reaction equation

HRID 1067466 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:15]2[O:14][CH2:13][C:12](=[O:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:2].[BrH:18].[NH+]1C=CC=CC=1.O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:15]2[O:14][CH:13]([Br:18])[C:12](=[O:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 21193670HCID 21193670, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 21193678HCID 21193678, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl[(3-oxo-2,3-dihydrobenzofuran-7-yl)oxy]acetate (1.00 g, 4.23 mmol) in chloroform (30 mL) was added pyridinium hydrobromide perbromide (1.35 g, 4.23 mmol) at 0° C. and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water. The organic layer was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide 1.20 g of ethyl[(2-bromo-3-oxo-2,3-dihydrobenzofuran-7-yl)oxy]acetate. A mixture of this compound (1.20 g, 3.80 mmol) and 1-phenyl-2-thiourea (580 mg, 3.80 mmol) in acetic acid (20 mL) was refluxed for 3 hours. The solvent was then distilled off under reduced pressure. To that residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5) to provide 180 mg of the title compound. Yield 12%.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c83330db65c44854b51adb72dca33477
Source dataset
uspto-grants-2001_06
Patent number
US06248766B1

Reaction notes

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