Sodium Hydroxide → 5-Bromo-7-fluoro-1-benzofuran-2-carboxylic acid

A solution of [(4-bromo-2-fluoro-6-formylphenyl)oxy]acetic acid (3.79 mmol) in acetic anhydride (10 mL) was treated with sodium acetate (11.37 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (20 mL) and was stirred at room temperature for 30 min. The solution was then further diluted with water (50 mL) and was extracted using hexanes. The aqueous phase was then acidified to pH˜1 using 1N aq HCl, and was extracted with ethyl acetate. The ethyl acetate layers were combined, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the title compound (0.47 g, 48% yield) which was used without further purification. MS(ES)+ m/e 258.5, 260.7 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.88 (d, J=1.77 Hz, 1H) 7.75 (dd, J=10.36, 1.77 Hz, 1H) 7.69 (d, J=2.53 Hz, 1H).

1. temperatureThe resulting solution was heated
2. temperatureto reflux
3. stirringwas stirred at room temperature for 30 min
4. extractionwas extracted
5. extractionwas extracted with ethyl acetate
6. washwashed with saturated aqueous sodium bicarbonate
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-a8b6ed4b33b445fe956fdf27263888eb

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802864B2