Stannous chloride dihydrate → 2-Amino-4-bromo-5-fluorophenol

Temperature

85 °C

Tin(II) chloride dihydrate (16.83 g, 74.6 mmol) was added to a solution of 4-bromo-5-fluoro-2-nitrophenol (4.4 g, 18.64 mmol) in ethanol (180 mL). The mixture was flushed with nitrogen and heated to 85° C. (oil bath temperature) for 1 day. The mixture was diluted with ethyl acetate (500 mL), saturated aqueous sodium bicarbonate (200 mL) was added with vigorous stirring. The mixture was filtered through celite and the celite pad was repeatedly washed with ethyl acetate. The two phases were separated and the organic phase was washed with brine. The combined aqueous phase was extracted with ethyl acetate. The combined organic phase was dried over MgSO4, filtered and concentrated to give 2-amino-4-bromo-5-fluorophenol. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.61 (br. s., 2H) 6.60 (d, J=10.11 Hz, 1H) 6.76 (d, J=7.33 Hz, 1H) 9.69 (br. s., 1 H).

1. customThe mixture was flushed with nitrogen
2. additionThe mixture was diluted with ethyl acetate (500 mL), saturated aqueous sodium bicarbonate (200 mL)
3. additionwas added with vigorous stirring
4. filtrationThe mixture was filtered through celite
5. washthe celite pad was repeatedly washed with ethyl acetate
6. customThe two phases were separated
7. washthe organic phase was washed with brine
8. extractionThe combined aqueous phase was extracted with ethyl acetate
9. dry with materialThe combined organic phase was dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-38db3c892cf74b92847489b3bffb93dd

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455522B2