Iodoethane → methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Iodoethane (2.04 mL, 25.54 mmol), was added to a stirred suspension of methyl 8-bromo-4-hydroxy-2-thioxo-2H-chromene-6-carboxylate (2.3 g, 7.30 mmol) and potassium carbonate (1.21 g, 8.76 mmol) in acetone (100 mL) under argon. The resulting mixture was stirred at 60° C. for 2 hrs. The mixture was concentrated in vacuo, and the residue was partioned between water and DCM. The aqueous layer was extracted into DCM, and the organic extracts were combined, washed with brine, dried over magnesium sulfate and evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% ethyl acetate in DCM. The solvent was evaporated to dryness to afford methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (1.8 g, 72%) as an orange solid. Mass Spectrum: M+H+ 343.
Workup
- concentrationThe mixture was concentrated in vacuo
- extractionThe aqueous layer was extracted into DCM
- washwashed with brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 10% ethyl acetate in DCM
- customThe solvent was evaporated to dryness
Sources & evidence
- ORD record
- ord-7b27232190d74e81a6b1aa808916a62f
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029374B2
Reaction notes
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