7,8-Dichloro-3,4-dihydro-2H-1-benzopyran-4-one → HCID 67123949, compound

HRID 871055Notes

Reaction equation

HRID 871055 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6](=[O:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[Br-:14].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)C.C(Cl)(Cl)Cl>[Br:14][CH:7]1[C:6](=[O:13])[C:5]2[C:10](=[C:11]([Cl:12])[C:2]([Cl:1])=[CH:3][CH:4]=2)[O:9][CH2:8]1

Participants

5

Reactant 2

HCID 126644077,8-Dichloro-3,4-dihydro-2H-1-benzopyran-4-oneHCID 21124087Pyridiniumtribromide

Product 1

HCID 67123949HCID 67123949, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 100 mg. (0.46 mmol) 7,8-dichlorochroman-4-one was dissolved in anhydrous ethanol (5 ml) and Chloroform (5 ml). To this solution was added pyridinium tribromide (0.442 g, 1.38 mmol, 3 equiv). The reddish brown mixture was heated with stirring at 50 C for 30 min. The reaction mixture was then cooled and the solvent was evaporated. Then water (20 ml) was added to the residue and it was then extracted with 20 ml of dichloromethane. The dichloromethane layer was then washed with 5% sodium bicarbonate solution followed by water (20 ml). The organic layer was then dried and the solvent was evaporated in vacuum to yield the crude product which was purified by column chromatography.

Workup

  1. additionA mixture of 100 mg
  2. temperatureThe reddish brown mixture was heated
  3. temperatureThe reaction mixture was then cooled
  4. customthe solvent was evaporated
  5. additionThen water (20 ml) was added to the residue and it
  6. extractionwas then extracted with 20 ml of dichloromethane
  7. washThe dichloromethane layer was then washed with 5% sodium bicarbonate solution
  8. customThe organic layer was then dried
  9. customthe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-3a86c43775ef46b78a4810b047208f6c
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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