Trifluoroacetic acid → HCID 21094333, compound

To a solution of 2-amino-5-nitrophenol (250 mg, 1.62 mmol) in 3 mL of trifluoroacetic acid stirred at 0° C., was added sodium borohydride (pellets, 375 mg, 9.91 mmol). The orange solution was allowed to slowly warm to rt and stirred for 12 h. The solution was diluted with 50 mL of water and cooled to 0° C. Solid potassium carbonate was then slowly added until the pH reached 7.The solution was extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with brine (25 mL), dried with anhydrous magnesium sulfate, filtered and concentrated to give an orange solid. Flash chromatography (7:3 hexanes:EtOAc) afforded 0.32 g (83%) of 2-(2,2,2-trifluoroethyl)amino-5-nitrophenol, a yellow solid. 1H NMR (400 MHz, acetone-d6) 9.48 (broad s, 1H), 7.79 (dd, 1H, J=9.1, 2.4), 7.67 (d, 1H, J=2.4), 6.96 (d, 1H, J=8.8), 6.20 (broad s, 1H), 4.26–4.18 (m, 2H).

1. temperaturecooled to 0° C
2. extractionwas extracted with ethyl acetate (2×100 mL)
3. washthe combined organic layers were washed with brine (25 mL)
4. dry with materialdried with anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give an orange solid

ORD record

ord-f53b7204e4e949f3923aa9515e7a70c4

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214690B2