Hydrochloric Acid → 7-Bromo-4H-1-benzopyran-4-one

HRID 1751401Notes

Reaction equation

HRID 1751401 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])/[CH:10]=[CH:11]/N(C)C)=[C:5]([OH:16])[CH:4]=1>ClCCl>[Br:2][C:3]1[CH:4]=[C:5]2[C:6]([C:9](=[O:15])[CH:10]=[CH:11][O:16]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11737295HCID 11737295, compound

Product 1

HCID 186867527-Bromo-4H-1-benzopyran-4-oneYield 100,000%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of concentrated hydrochloric acid (30 mL) was added to a solution of (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one (10.4 g, 38.5 mmol) in dichloromethane (250 mL). The mixture was heated at reflux for 30 minutes and cooled to room temperature. The aqueous phase was extracted with dichloromethane (20 mL). The combined organic phases were washed with saturated sodium bicarbonate (50 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to yield 7-bromo-4H-chromen-4-one (8.7 g, 38.5 mol, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. extractionThe aqueous phase was extracted with dichloromethane (20 mL)
  4. washThe combined organic phases were washed with saturated sodium bicarbonate (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7a1acb49fd9f44058ade568147b52fcd
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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