Hydrogen Bromide → HCID 22033294, compound

HRID 1859338Notes

Reaction equation

HRID 1859338 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:22])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:22])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 109799547-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one

Product 1

HCID 22033294HCID 22033294, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To acetic acid solution (15 ml) of 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (2.82 g, 8.99 mmol) was added aqueous 48% HBr solution (13 ml) and the mixture was heated under refluxing for 24 hours. The reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified with silica gel column chromatography (ethyl acetate:hexane=2:1) to obtain 2.46 g (yield: 96%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for 24 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe crude product thus obtained
  9. customwas purified with silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-ec9218a9fb2e40389b1958efa2e9c0ca
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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