Sodium Hydroxide → 2-Amino-4-fluorophenol

Temperature

70 °C

Tin(II) chloride (12.1 g, 63.6 mmol) was added to a solution of 4-fluoro-2-nitrophenol (2.00 g, 12.7 mmol) in EtOH (45 mL), and the reaction mixture was heated to 70° C. After 2 h, the reaction mixture was allowed to cool to rt and was poured onto ice (˜200 mL). After warming to rt, the pH was adjusted to ˜9 with 2 N aqueous NaOH, and the mixture was filtered. The filtrate was extracted with EtOAc (3×), and the combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 1.21 g (75%) of the title compound. LC-MS: RT=4.48 min., [M+H]+=128.0.

1. temperatureto cool to rt
2. additionwas poured onto ice (˜200 mL)
3. temperatureAfter warming to rt
4. filtrationthe mixture was filtered
5. extractionThe filtrate was extracted with EtOAc (3×)
6. dry with materialthe combined EtOAc extracts were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-c64d0ba619ef4540ae9434e850b06c81

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822472B2