Nitric Acid → 5'-Bromo-2'-hydroxy-3'-nitroacetophenone

HRID 1603875Notes

Reaction equation

HRID 1603875 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[N+:12]([O-])([OH:14])=[O:13]>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]([C:4]1[C:5]([OH:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=[C:8]([Br:10])[CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 6890715'-Bromo-2'-hydroxy-3'-nitroacetophenone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 5-bromo-2-hydroxyacetophenone (23.7 g, 0.110 mol) in carbon tetrachloride (90 ml) was added with concentrated nitric acid (17.2 ml). The mixture was left under stirring at 75° C. for 50 minutes, then left to cool at room temperature. The precipitated solid was recovered by filtration washing with cold carbon tetrachloride. After drying under vacuum, 20.9 g of the title product were obtained as a light yellow solid (73% yield).

Workup

  1. waitThe mixture was left
  2. waitleft
  3. temperatureto cool at room temperature
  4. filtrationThe precipitated solid was recovered by filtration
  5. washwashing with cold carbon tetrachloride
  6. customAfter drying under vacuum

Sources & evidence

ORD record
ord-422c6711dc4345e29570c538264beb4c
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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