Acetic Acid → 3-Fluoro-2-hydroxy-5-nitrobenzaldehyde

HRID 708865Notes

Reaction equation

HRID 708865 reaction equation
[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(O)(=O)C.[N+:15]([O-])([OH:17])=[O:16]>>[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 152945723-Fluoro-2-hydroxy-5-nitrobenzaldehydeYield 83%

Conditions

Temperature
0 °C

Procedure

To a flask with 3-fluoro-2-hydroxybenzaldehyde (5.00 g, 35.7 mmol) in acetic acid (10 mL, 175 mmol), was added nitric acid (conc., 10 mL, 244 mmol) at 0° C. The mixture was stirred 0° C. for 30 min, quenched with ice, extracted with EtOAc (3×30 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated to give 17C (5.457 g, 29.5 mmol, 83% yield) as a yellow solid.

Workup

  1. customquenched with ice
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c9d3098445be45abbc2dfbc9047f900d
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

Loading…