4-BROMO-2-HYDROXYBENZONITRILE synthesis
- 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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288067-35-6
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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
105942-08-3
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288067-35-6
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330793-38-9
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288067-35-6
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591-20-8
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288067-35-6
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