Nitric Acid → 4-Fluoro-3-nitrobenzaldehyde

HRID 1898320Notes

Reaction equation

HRID 1898320 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11]>OS(O)(=O)=O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 680234-Fluorobenzaldehyde

Product 1

HCID 5981294-Fluoro-3-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution of 4-fluorobenzaldehyde (1 g) in conc. H2SO4 was added conc. HNO3 drop-wise at 0° C. The reaction mass was stirred at 0° C. for 1 h. The reaction mass was quenched in water and filtered to afford 1.2 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.82 (t, J=9.3 Hz, 1H), 8.32 (m, 1H), 8.68 (d, J=7.2 Hz, 1H), 10.06 (s, 1H); MS [M+H]+: 184.08.

Workup

  1. customdrop-wise at 0° C
  2. customThe reaction mass was quenched in water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-40078b18ff9e46fc9a3b3e21bb1a794c
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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