Triethylamine → 3-Amino-4-fluorophenol

To a solution of 2-chloro-4-fluoro-5-nitrophenol (3.20 g, 16.7 mmol) in methanol (60 mL) was added 20 wt % palladium hydroxide on carbon (1.60 g) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 8 hr under hydrogen atmosphere. After nitrogen replacement, triethylamine (2.32 mL, 16.7 mmol) was added to the reaction mixture, and the mixture was filtered through a kiriyama funnel. Saturated brine was added to the filtrate, and the mixture was extracted twice with diethyl ether. The extract was dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was recrystallized from diethyl ether/hexane to give the title compound (1.40 g, 66%) as pale-brown crystals.

1. filtrationthe mixture was filtered through a kiriyama funnel
2. additionSaturated brine was added to the filtrate
3. extractionthe mixture was extracted twice with diethyl ether
4. dry with materialThe extract was dried over anhydrous magnesium sulfate
5. filtrationfiltrated
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was recrystallized from diethyl ether/hexane

ORD record

ord-d5d7e31587f9458291b600908006e48a

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273741B2