Potassium Nitrate → 5-Bromo-2-nitrobenzaldehyde

HRID 506852Notes

Reaction equation

HRID 506852 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[N+:10]([O-])([O-:12])=[O:11].[K+]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:4]([CH:3]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 765833-Bromobenzaldehyde

Product 1

HCID 972335-Bromo-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sulfuric acid (108 mL) and 3-bromobenzaldehyde (25 g, 0.135 mol) were cooled to 0° C. in a flask. Potassium nitrate (14.3 g, 0.14 mol) was added to the resulting mixture, portion wise over 1 h. The resulting mixture was stirred an additional 2 h at 0° C. For work up, the resulting mixture was poured into 2 L of ice and then filtered to yield a solid. The solid was purified by silica chromatography (330 g, 30% Et2O/heptane) to yield a residue, which was recrystallized from EtOAc/heptane to yield a solid.

Workup

  1. filtrationfiltered
  2. customto yield a solid
  3. customThe solid was purified by silica chromatography (330 g, 30% Et2O/heptane)
  4. customto yield a residue, which
  5. customwas recrystallized from EtOAc/heptane
  6. customto yield a solid

Sources & evidence

ORD record
ord-e7383bb14d994ba68ed481daa16f094e
Source dataset
uspto-grants-2010_08
Patent number
US07786116B2

Reaction notes

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