Potassium Hydroxide → HCID 90404004, compound

Temperature

2.5 °C

4-Bromo-5-fluoro-2-nitroaniline (8.5 g, 36 mmol) was stirred in 200 mL ethanol and treated with 45% KOH solution (4.5 g, 36 mmol) to produce a dark solution. This solution was cooled to 0-5° C. and treated dropwise with 6% NaOCl solution (84 g, 68 mmol) over 20 min while maintaining the temperature below 10° C. After 90 min, the mixture was diluted with 300 mL water and extracted twice with 200 mL portions of ethyl acetate. The combined extracts were washed with 30 mL saturated NaCl, dried (Na2SO4) and evaporated. The crude material was chromatographed on silica gel with a 0-30% ethyl acetate-hexane gradient to give the title compound as pale yellow solid (3.5 g, 42%): mp 87-89° C.; 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.23 (s, 1H); 19F NMR (376 MHz, CDCl3) δ −96.03; EIMS m/z 232.

1. customto produce a dark solution
2. temperaturewhile maintaining the temperature below 10° C
3. extractionextracted twice with 200 mL portions of ethyl acetate
4. washThe combined extracts were washed with 30 mL saturated NaCl
5. dry with materialdried (Na2SO4)
6. customevaporated
7. customThe crude material was chromatographed on silica gel with a 0-30% ethyl acetate-hexane gradient

ORD record

ord-c31f80c648d247d7aac168bd36196c1c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006250B2