Nitric Acid → 5-Bromo-2-nitrobenzaldehyde

HRID 2272252Notes

Reaction equation

HRID 2272252 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-])([OH:12])=[O:11]>>[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

3

Reactant 2

HCID 944Nitric AcidHCID 765833-Bromobenzaldehyde

Product 1

HCID 972335-Bromo-2-nitrobenzaldehydeYield 48%

Procedure

To ice cold conc. sulphuric acid (400 mL) was added fuming nitric acid (200 mL) dropwise followed by 3-bromobenzaldehyde (i) (100 g, 0.540 mol) dropwise over 15 min. The reaction mixture was stirred for 10 min and then poured carefully over ice-water. The resulting solids were filtered and then purified by flash column chromatography on silica gel, eluting with EtOAc:n-hexane (gradient elution from 1% to 20% v/v) to give (ii) (60 g, 48%).

Workup

  1. filtrationThe resulting solids were filtered
  2. custompurified by flash column chromatography on silica gel
  3. washeluting with EtOAc
  4. washn-hexane (gradient elution from 1% to 20% v/v)

Sources & evidence

ORD record
ord-4aa0f174512b43f7bfc2ff59acf95ab4
Source dataset
uspto-grants-2015_09
Patent number
US09120775B2

Reaction notes

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