Nitric Acid → 4-Fluoro-3-nitrobenzaldehyde

HRID 64051

Reaction equation

HRID 64051 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1>S(=O)(=O)(O)O>[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 680234-Fluorobenzaldehyde

Product 1

HCID 5981294-Fluoro-3-nitrobenzaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

Nitration mixture (sulfuric acid 40 ml+nitric acid 5.5 ml) was added dropwise to 4-fluorobenzaldehyde (10 g, 80.57 mmol) at 0° C. and the mixture was stirred at 5° C. for 20 min and at RT for 1 h. The mixture was quenched by the addition of crushed ice. The precipitate formed was filtered and was washed repeatedly with water to give white solid. The solid was dried under vacuum to give the product in 77% yield (10.5 g). 1H NMR (300 MHz, CDCl3): δ 10.04 (s, 1H), 8.58 (dd, 1H), 8.22-8.18 (m, 1H), 7.5 (t, 1H).

Workup

  1. customThe mixture was quenched by the addition of crushed ice
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwas washed repeatedly with water
  5. customto give white solid
  6. customThe solid was dried under vacuum
  7. customto give the product in 77% yield (10.5 g)

Sources & evidence

ORD record
ord-102b47a80918421a8aefdc9de808d131
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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