3-Nitrobenzoic acid → 3-Bromo-5-nitrobenzoic acid

HRID 1766384Notes

Reaction equation

HRID 1766384 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[Br:13]N1C(=O)CCC1=O>FC(F)(F)C(O)=O.S(=O)(=O)(O)O>[Br:13][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 84973-Nitrobenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 2393363-Bromo-5-nitrobenzoic acidYield 72%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-nitrobenzoic acid (16.7 g, 100 mmol) in trifluoroacetic acid (50 mL) and sulfuric acid (20 mL) was stirred at 50° C., and N-bromosuccinimide (26.7 g, 150 mmol) was added in three portions over 3 hours. The mixture was stirred for 16 hours and then cooled to room temperature. The mixture was then poured into ice water (200 mL) and extracted three times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was recrystallized from dichloromethane to provide a white solid (17.7 g, 72%). 1H NMR (300 MHz, DMSO-d6) δ13.8 (bs, 1H), 8.60 (s, 1H), 8.55 (s, 1H), 8.37 (s, 1H).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-3b43dada55c040a5a5f5b1f875dc3a00
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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