Ethanol → 4-Bromo-2-ethoxy-benzoic acid ethyl ester

Temperature

0 °C

Sodium (1.815 g, 78.9 mmol, Aldrich) was cut into small pieces and added to ethanol (100 mL). After all the pieces were dissolved, the clear solution was added to a solution of ethyl 4-bromo-2-fluoro-benzoate (13 g, 52.6 mmol) in ethanol (20 mL) cooled to 0° C. The ice bath was then removed and the mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated in vacuo, and the residue was taken in water and 20% ethyl acetate-hexane. The organic layer was washed with saturated solution of sodium bicarbonate, brine, and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (120 g of silica gel, eluting with 10-15% ethyl acetate in hexane) gave 4-bromo-2-ethoxy-benzoic acid ethyl ester as white solids (11.020 g, 77%).

1. dissolutionAfter all the pieces were dissolved
2. customThe ice bath was then removed
3. concentrationThe reaction mixture was concentrated in vacuo
4. washThe organic layer was washed with saturated solution of sodium bicarbonate, brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe solids were filtered off
7. concentrationthe filtrate was concentrated in vacuo
8. customPurification of the crude residue
9. washby flash chromatography (120 g of silica gel, eluting with 10-15% ethyl acetate in hexane)

ORD record

ord-9e17f62b135d4aabaa0fe493f69ad151

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851626B2