5-Fluoro-2-nitrophenol → 2-Amino-5-fluorophenol

A suspension of 3-fluoro-6-nitrophenol (500 mg, 3.18 mmol) and zinc (2.10 g, 31.8 mmol) in acetic acid (7.3 mL) was stirred overnight at room temperature. The reaction mixture was filtered through celite and washed with DCM. After evaporation and distillation under vacuum (2.10−2 mbar) of the solvents, the residue was dissolved in DCM. The organic phase was washed with a saturated solution of NaHCO3 and brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5) to yield 177 mg (1.39 mmol, 44%) of 2-amino-5-fluorophenol as an orange solid.

1. filtrationThe reaction mixture was filtered through celite
2. washwashed with DCM
3. customAfter evaporation and distillation under vacuum (2.10−2 mbar) of the solvents
4. dissolutionthe residue was dissolved in DCM
5. washThe organic phase was washed with a saturated solution of NaHCO3 and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customThe crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5)

ORD record

ord-da403d56fbfa47369a54ed804e74820a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101637B2