Nitric Acid → 2,6-Difluoro-4-methoxy-3-nitrobenzaldehyde

HRID 79042Notes

Reaction equation

HRID 79042 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([F:16])[C:7]=1[CH:8]=[O:9]>S(=O)(=O)(O)O>[F:5][C:6]1[C:13]([N+:1]([O-:4])=[O:2])=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([F:16])[C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 37037132,6-Difluoro-4-methoxybenzaldehyde

Product 1

HCID 583743662,6-Difluoro-4-methoxy-3-nitrobenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of cold (−5° C.) nitric acid (2.7 mL) was added concentrated sulfuric acid (1.75 mL, 32 mmoL) dropwise keeping the temperature below 5° C. The solution was added to a cooled solution of 2,6-difluoro-4-methoxy benzaldehyde (5.0 g, 29 mmoL) in sulfuric acid (20 mL) over 15 minutes keeping the temperature below 5° C. After stirring at 0° C. for 2 hours the orange solution was poured on to ice, the white precipitate which formed was collected by filtration to give the title compound as a white solid (6.33 g, 100%). 1H NMR (CDCl3) 10.20 (1 H, t, J=1.17 Hz), 6.69 (1 H, dd, J=11.68, 1.93 Hz), 4.03 (3 H, s).

Workup

  1. customthe temperature below 5° C
  2. customthe temperature below 5° C
  3. additionwas poured on to ice
  4. customthe white precipitate which formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d369b5bfee144255ae51b361aa4cc6a4
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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