Water → HCID 21193678, compound

HRID 2228718Notes

Reaction equation

HRID 2228718 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[O:4][CH2:3]1.[BrH:18].[NH+]1C=CC=CC=1.O>C(Cl)(Cl)Cl>[Br:18][CH:3]1[C:2](=[O:1])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[O:4]1

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-97e61d1bccf0476988aa33e18f7d684e
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

Loading…