Hydrogen Bromide → HCID 22033294, compound

HRID 1792314Notes

Reaction equation

HRID 1792314 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 92.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (2.27 g, 7.22 mmol) in acetic acid (75 ml) was added 48% aqueous HBr solution (75 mg), which was then heated under reflux for 1 day. The reaction mixture was extracted with diethyl ether. The organic layer was washed with saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated. Then, the residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=7:3 and 1:1) to give the title compound (1.92 g, yield 92%).

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 1 day
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1fa491b162164f098d0ec14018659b67
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…