Iodoethane → methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate

HRID 41214Notes

Reaction equation

HRID 41214 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=[C:9]2[C:14]=1[O:13][C:12](=[S:15])[CH:11]=[C:10]2[OH:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:4][C:5]1[CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=[C:9]2[C:14]=1[O:13][C:12]([S:15][CH2:2][CH3:3])=[CH:11][C:10]2=[O:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178497027HCID 178497027, compound

Product 1

HCID 58235026methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Iodoethane (37.1 mL, 463.51 mmol) was added in one portion to a stirred suspension of methyl 8-bromo-4-hydroxy-2-thioxo-2H-chromene-6-carboxylate (48.69 g, 154.5 mmol) and potassium carbonate (21.35 g, 154.50 mmol) in acetone (490 mL). The resulting suspension was stirred at reflux for 1 h under nitrogen in a flask equipped with a bleach trap. The reaction mixture was concentrated, the residue was diluted with DCM (980 mL)/water (490 mL). The phases were separated and the aqueous layer was extracted with DCM (490 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated. The residue was triturated with petroleum ether, filtered and dried under vacuum to give methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (52.9 g, 100%) as a pale brown solid. Mass Spectrum: m/z [M+H]+=345

Workup

  1. temperatureat reflux for 1 h under nitrogen in a flask
  2. customequipped with a bleach trap
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with DCM (980 mL)/water (490 mL)
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted with DCM (490 mL)
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was triturated with petroleum ether
  11. filtrationfiltered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-840448d82c7648e199e78605a568968f
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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