Hydrogen Bromide → 3-Bromo-5-nitrobenzoic acid

HRID 1612430Notes

Reaction equation

HRID 1612430 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].N([O-])=O.[Na+].O.[BrH:19]>>[Br:19][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

5

Reactant 4

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 2393423-Amino-5-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 2393363-Bromo-5-nitrobenzoic acid

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-amino-5-nitro-benzoic acid (8.0 g) in 48% aqueous HBr (90 ml) at 0° C. was added sodium nitrite (4.0 g) over 15 minutes. The resulting solution of diazonium salt was added to CuBr (4.0 g) in 48% HBr (10 ml) at 60–70° C. at such a rate to maintain the temperature at 60–70° C. After completion of the addition, the mixture was warmed to 70° C. for 45 minutes. The mixture was cooled to room temperature, water (500 ml) was added and the product was extracted into ether (3×). The combined extracts were washed with water (2×), dried over sodium sulfate and evaporated to give a beige solid, 10.53 g.

Workup

  1. temperatureto maintain the temperature at 60–70° C
  2. additionAfter completion of the addition
  3. temperatureThe mixture was cooled to room temperature
  4. extractionthe product was extracted into ether (3×)
  5. washThe combined extracts were washed with water (2×)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give a beige solid, 10.53 g

Sources & evidence

ORD record
ord-a3de5c2f06dd4b098c597cd0e998fa61
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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