4-Hydroxy-3-nitrobenzonitrile → Benzonitrile, 3-bromo-4-hydroxy-5-nitro-

HRID 2218952Notes

Reaction equation

HRID 2218952 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Br:13]([O-])(=O)=O.[K+]>OS(O)(=O)=O>[Br:13][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([N+:10]([O-:12])=[O:11])[C:2]=1[OH:1])[C:6]#[N:7]

Participants

4

Reactant 2

HCID 767584-Hydroxy-3-nitrobenzonitrileHCID 23673461Potassium Bromate

Product 1

HCID 3014048Benzonitrile, 3-bromo-4-hydroxy-5-nitro-Yield 57%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 5 g (30.5 mmol) of 4-hydroxy-3-nitrobenzonitrile in H2SO4 solution (50 mL of concentrated H2SO4+50 mL of H2O) at 25° C., 7.9 g (47.3 mmol) of potassium bromate were added in small portions cooling the flask with an ice-bath and maintaining the temperature between 25 and 35° C. After the addition was completed, the reaction was stirred at room temperature for 22 h and then filtered. The pale yellow solid was washed with water and dried to give 4.2 g (57%) of the title compound. M.p.: 162-164° C.; 1H NMR (CD3OD) δ 8.54 (d, 1H, J=2.0 Hz, H-6), 8.32 (d, 1H, J=2.0 Hz, H-2); 13C NMR (DMSO-d6) δ 153.9 (C-4), 140.8 (C-2), 138.2 (C-5), 130.1 (C-6), 117.0 (CN), 115.9 (C-3), 101.6 (C-1).

Workup

  1. temperaturecooling the flask with an ice-bath
  2. temperaturemaintaining the temperature between 25 and 35° C
  3. additionAfter the addition
  4. filtrationfiltered
  5. washThe pale yellow solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-445f3c8edc84448489d7bfcb115e195b
Source dataset
uspto-grants-2008_08
Patent number
US07414036B2

Reaction notes

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