Nitric Acid → 4-Bromo-2-fluoro-5-nitrobenzaldehyde

HRID 1966311Notes

Reaction equation

HRID 1966311 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([F:14])[CH:7]=1>S(=O)(=O)(O)O>[Br:5][C:6]1[C:13]([N+:1]([O-:4])=[O:2])=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([F:14])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 184555954-Bromo-2-fluoro-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (25 mL) is added dropwise to a solution of 4-bromo-2-fluorobenzaldehyde (5.12 g, 25.2 mmol) in sulfuric acid (25 mL). The mixture is stirred for 2 hours and then is poured over ice. Product is extracted into MTBE (100 mL). The organic layer is washed with saturated aqueous NaHCO3 (100 mL), dried (Na2SO4), and evaporated yielding 5.98 g of yellow solid. 1H NMR (DMSO-d6) δ 10.13, 8.49, 8.22.

Workup

  1. additionis poured over ice
  2. extractionProduct is extracted into MTBE (100 mL)
  3. washThe organic layer is washed with saturated aqueous NaHCO3 (100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-80c90b47904e42f0a92f4d2eb3cfc562
Source dataset
uspto-grants-2013_04
Patent number
US08420646B2

Reaction notes

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