Nitric Acid → 5'-Fluoro-2'-hydroxy-3'-nitroacetophenone

HRID 325744

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[N+:12]([O-])([OH:14])=[O:13].O>S(=O)(=O)(O)O>[CH3:1][C:2]([C:4]1[C:5]([OH:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=[C:8]([F:10])[CH:9]=1)=[O:3]

Participants

Conditions

Temperature: -20 °C

Procedure

5-Fluoro-2-hydroxyacetophenone (20.0 g) was dissolved in concentrated sulphuric acid (150 ml), and the mixture was cooled to -20° C. A mixture of concentrated nitric acid (17.0 ml; s.g. 1.42) in concentrated sulphuric acid (18.0 ml) was then added to it, dropwise with stirring, keeping the temperature of the reaction mixture between -15° and -5° C. The reaction mixture was then allowed to warm up to -5° C. and was poured into iced water (2 liters). The yellow precipitated product was filtered off and recrystallised from ethanol to give 5-fluoro-2-hydroxy-3-nitroacetophenone (11.9 g), m.p. 87°-90° C.

Workup

additionwas then added to it
customthe temperature of the reaction mixture between -15° and -5° C
temperatureto warm up to -5° C.
filtrationThe yellow precipitated product was filtered off
customrecrystallised from ethanol

Sources & evidence

ORD record: ord-1cbee42d0ddd47a0969e630c7e489cba
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04442115

Linked notes

Loading…