ChemicalBook CAS DataBase List 4-BROMO-2-HYDROXYBENZONITRILE

4-BROMO-2-HYDROXYBENZONITRILE synthesis

4synthesis methods

Product Name:4-BROMO-2-HYDROXYBENZONITRILE
CAS Number:288067-35-6
Molecular formula:C7H4BrNO
Molecular Weight:198.02

179897-89-3
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$10.00/5g

288067-35-6
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$5.00/250mg

Yield:288067-35-6 81%

Reaction Conditions:

with sodium hydroxide;potassium acetate;18-crown-6 ether in ethyl acetate;acetonitrile

Steps:

1.a a
a 2-Hydroxyl-4-bromobenzonitrile A mixture of 2-fluoro-5-bromobenzonitrile (30 g, 152.3 mmole), potassium acetate (222.4 g, 228.5 mmole), and 18-crown-6 ether (60.4 g, 288.5 mmole) in MeCN (400 mL) was heated at reflux in 36 h. The mixture was cooled, added 2.5 N NaOH (200 mL), stirred at RT overnight. The mixture was extracted with ether (discarded). The aqueous layer was acidified with 6N HCl, extracted with EtOAc, dried over MgSO₄, concentrated, purified by flash column chromatography (40% EtOAc/Hex) to give a light yellow foam (24.45 g, 81%). ¹H-NMR (300 MHz, DMSO-d₆): δ7.13 (dd, J=1.7, 8.3 Hz, 1H), 7.17 (d, J=1.7 Hz, 1H), 7.61 (d, J=8.3 Hz, 1H).

References:

SmithKline Beecham Corporation US6417215, 2002, B1

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105942-08-3 Synthesis