Bromide ion → 3-Bromo-5-nitrobenzoic acid

HRID 1664222Notes

Reaction equation

HRID 1664222 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[BrH:14].N([O-])=O.[Na+].[Br-]>O.C(OCC)C>[Br:14][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 260Hydrogen Bromide2×HCID 2393423-Amino-5-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 2393363-Bromo-5-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

To the solution of 7.92 g (43 mmol) 3-amino-5-nitro-benzoic acid in 4 ml water in an ice bath 48.8 ml (434 mmol, 10 eq) of aq 48% HBr are added. A saturated aqueous solution of 4.05 g (59 mmol, 1.35 eq) sodium nitrit is added over 10 min. The obtained solution is added to the solution of 9.36 g (65 mmol, 1.5 eq) cupper bromide in 48.8 ml (434 mmol, 10 eq) of aq 48% HBr at 70° C. The mixture is heated for 45 min at 70° C. After cooling to rt diethylether is added and the organic layer is washed with water until neutral pH is reached. Drying over sodium sulfate and evaporation of the solvent at reduced pressure to give the product as yellow solid.

Workup

  1. additionis added
  2. washthe organic layer is washed with water until neutral pH
  3. dry with materialDrying over sodium sulfate and evaporation of the solvent at reduced pressure

Sources & evidence

ORD record
ord-b967bbc14b4b45fdbed66c8d42fb1a3e
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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