Nitric Acid → 2-Bromo-5-nitrobenzaldehyde

HRID 973377Notes

Reaction equation

HRID 973377 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]>OS(O)(=O)=O>[Br:5][C:6]1[CH:13]=[CH:12][C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 811292-Bromobenzaldehyde

Product 1

HCID 111389422-Bromo-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A nitrating acid prepared at -10° C. by adding 55 ml of concentrated H2SO4 to 20 ml of 98 percent HNO3 was added dropwise, in the course of 60 minutes, to a solution of 63.4 g (0.34 mole) of 2-bromobenzaldehyde in 110 ml of concentrated H2SO4 at -5° C. Stirring was continued for a further 45 minutes, after which the reaction mixture was poured onto 550 g of ice, and the precipitated solid was filtered off under suction, washed with water, then with 10 percent strength Na2CO3 solution and again with water. Drying under reduced pressure at 50° C. gave 72 g (92% of theory) of product as a yellow solid of melting point 86°-88° C.

Workup

  1. customA nitrating acid prepared at -10° C.
  2. filtrationthe precipitated solid was filtered off under suction
  3. washwashed with water
  4. customDrying under reduced pressure at 50° C.
  5. customgave 72 g (92% of theory) of product as a yellow solid of melting point 86°-88° C.

Sources & evidence

ORD record
ord-5dd13747f38b4b889aca6ae2c7e55e8d
Source dataset
uspto-grants-1991_11
Patent number
US05062884

Reaction notes

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