Methyl iodide → Methyl 4-bromo-2-(2-methylpropoxy)benzoate

To a solution of 4-bromo-2-isobutoxybenzoic acid (14.0 g) in N,N-dimethylformamide (70 ml) were added dipotassium carbonate (14.2 g) and iodomethane (4.79 ml). The mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered and the filtrate was extracted with ethyl acetate-hexane (1/1, 600 ml) and washed with water (500 ml). The water layer was extracted with ethyl acetate-hexane (1/1, 200 ml) and the extract was washed with water (200 ml). The combined organic layer was washed with brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave methyl 4-bromo-2-isobutoxybenzoate (12.0 g) as a pale yellow oil.

1. filtrationThe reaction mixture was filtered
2. extractionthe filtrate was extracted with ethyl acetate-hexane (1/1, 600 ml)
3. washwashed with water (500 ml)
4. extractionThe water layer was extracted with ethyl acetate-hexane (1/1, 200 ml)
5. washthe extract was washed with water (200 ml)
6. washThe combined organic layer was washed with brine
7. dry with materialdried over magnesium sulfate
8. filtrationFiltration
9. customfollowed by evaporation under reduced pressure

ORD record

ord-f72d54970fd6479199b19c206fa32afb

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417060B2