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

HRID 1271894Notes

Reaction equation

HRID 1271894 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-fb6d761060f449d8bd9264dadaef266b
Source dataset
uspto-grants-2007_04
Patent number
US07208490B2

Reaction notes

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