Hydrochloric Acid → 4-ethyl-3-fluorophenol

2-Fluoro-4-hydroxyacetophenone (15.14 g, 100 mmol) and zinc dust (19.61 g, 300 mmol) were suspended in 50 mL of H2O with stirring. Concentrated HCl (37%, 50 mL, 610 mmol) were added and the mixture was heated to reflux for six h. The reaction was cooled to rt, and diethyl ether was added. The mixture was saturated with NaCl, and filtered through celite washing with diethyl ether. The filtrate was poured into brine, and the layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 7.24 g (52%) of the title compound of step A. 1H NMR (400 MHz, DMSO-d6) δ 9.53 (s, 1H), 7.00 (t, J=8.8 Hz, 1H), 6.52-6.40 (m, 2H), 2.44 (q, J=7.5 Hz, 2H), 1.06 (t, J=7.5 Hz, 3H).

1. temperaturethe mixture was heated
2. temperatureto reflux for six h
3. filtrationfiltered
4. washthrough celite washing with diethyl ether
5. additionThe filtrate was poured into brine
6. customthe layers were separated
7. extractionThe aqueous layer was extracted with diethyl ether
8. dry with materialThe combined organic layers were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography

ORD record

ord-c61be6fd89164ba2a455edb51e3c3fd5

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093239B2