ChemicalBook CAS DataBase List 5-BROMO-2-HYDROXYBENZONITRILE

5-BROMO-2-HYDROXYBENZONITRILE synthesis

11synthesis methods

Product Name:5-BROMO-2-HYDROXYBENZONITRILE
CAS Number:40530-18-5
Molecular formula:C7H4BrNO
Molecular Weight:198.02

1761-61-1

40530-18-5

Synthesis of 5-bromo-2-hydroxybenzonitrile: To a solution of 5-bromosalicylaldehyde (80.0 g, 0.40 mol) in formic acid was added hydroxylamine hydrochloride (36.0 g, 0.52 mol) and sodium form (37.0 g, 0.52 mol) in sequence. The reaction mixture was stirred at 100 °C for 7 hours. After completion of the reaction, the solvent was removed by evaporation and the residue obtained was dissolved in ethyl acetate. The organic layer was washed with water and dried. The solvent was again removed by evaporation and petroleum ether was added to the residue, and the precipitated crystals were filtered to give 5-bromo-2-hydroxybenzonitrile (75.2 g, 95% yield).1H-NMR (DMSO-d6) δ: 6.98 (d, J = 8.9 Hz, 1H), 7.65 (dd, J = 8.9,2.4 Hz, 1H), 7.86 (d, J = 2.4 Hz , 1H), 11.41 (s, 1H).

1761-61-1
391 suppliers
$5.00/5g

40530-18-5
184 suppliers
$15.00/1g

Yield:40530-18-5 95%

Reaction Conditions:

with formic acid;hydroxylamine hydrochloride;sodium formate at 100; for 7 h;

Steps:

1

5-Bromo-2-hydroxybenzonitrile; To a solution of 5-bromosalicylaldehyde (80.0 g, 0.40 mol) in formic acid were added hydroxylamine hydrochloride (36.0 g, 0.52 mol) and sodium format (37.0 g, 0.52 mol) followed by stirring at 100°C for 7 hours. Ethyl acetate was added to the residue prepared by evaporation of the solvent, the mixture was washed with water and then an organic layer was dried. Petroleum ether was added to the residue prepared by evaporation of the solvent and the crystals separated out therefrom were filtered to give the title compound (75.2 g, 95%). ¹H-NMR (DMSO-d₆) δ: 6.98 (d, J=8.9 Hz, 1H), 7.65 (dd, J=8.9, 2.4 Hz, 1H), 7.86 (d, J=2.4 Hz, 1H), 11.41 (s, 1H).

References:

EP2128136,2009,A1 Location in patent:Page/Page column 7