Water → 4-Amino-2-iodophenol

Temperature

75 °C

To a yellow suspension of 2,6-diiodo-4-nitrophenol (2.5 g, 6.44 mmol) in 50 mL of 25% NaOH, was added sodium dithionite (36 g) and the reaction mixture was heated and stirred at 75° C., until it was tuned white. After the reaction mixture was cooled to room temperature, 50 mL deionized water was added, and extracted with ethyl acetate (50 mL×5). The combined extracts were washed with water (30 mL×3), brine (30 mL) and dried with Na2SO4. Removed the solvent to give a brown oil, which was purified by flushing chromatography column, eluant with system A Hexane/ethyl acetate (6/1), then system B Hexane/ethyl acetate (3/1) to give a brown solid (0.27 g). 1H-NMR(300 MHz, DMSO): δ9.23 (s, 1H), 7.00˜6.99 (d, 1H), 6.64˜6.61 (d, 1H), 6.52˜6.48 (d, 1H), 5.25 (bs, 2H).

1. temperaturethe reaction mixture was heated
2. temperatureAfter the reaction mixture was cooled to room temperature
3. additionwas added
4. extractionextracted with ethyl acetate (50 mL×5)
5. washThe combined extracts were washed with water (30 mL×3), brine (30 mL)
6. dry with materialdried with Na2SO4
7. customRemoved the solvent
8. customto give a brown oil, which
9. customwas purified
10. customby flushing chromatography column, eluant with system A Hexane/ethyl acetate (6/1)

ORD record

ord-f8838971a7cc492591f19edf44fcaff7

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08460635B2