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

HRID 1947362Notes

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

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 pardoned 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-bf9fc021cafd426fa28d468f88008d7e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399460B2

Reaction notes

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