Potassium Carbonate → Methyl 5-bromo-3-methylbenzofuran-2-carboxylate

To a solution (100 mL) of 1-(5-bromo-2-hydroxyphenyl)ethanone (10.0 g) in N,N-dimethylformamide were added methyl bromoacetate (4.85 mL) and potassium carbonate (12.9 g), and the mixture was stirred overnight at room temperature. The insoluble material was filtered off, 1,8-diazabicyclo[5.4.0]undec-7-ene (6.95 mL) was added to the filtrate, and the mixture was stirred at 120° C. for 2 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to give the title object compound (6.06 g, 48%) as a pale-brown solid.

1. filtrationThe insoluble material was filtered off
2. addition1,8-diazabicyclo[5.4.0]undec-7-ene (6.95 mL) was added to the filtrate
3. stirringthe mixture was stirred at 120° C. for 2 hr
4. addition1N Hydrochloric acid was added
5. customto quench
6. customthe reaction
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with saturated brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

ORD record

ord-aa5ea168d74447afbe478e5a22492aad

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2