Water → Methyl 5-bromo-3-methyl-2-furoate

Temperature

0 °C

To a solution of methyl 3-methylfuran-2-carboxylate (5.6 g) in chloroform (40 mL) was added dropwise bromine (2.3 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min, at room temperature for 1 hr, and at 50° C. overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 10% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (5.3 g, 60%) as a white solid.

1. additionafter the completion of the dropwise addition
2. customat 50° C.
3. customovernight
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 10% ethyl acetate/hexane)
9. customcrystallized from ethyl acetate/hexane

ORD record

ord-1977b3468bdc4a8b9091c8e9f4d1dacd

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309580B2