ChemicalBook CAS DataBase List 2-BROMO-5-METHOXYBENZONITRILE

2-BROMO-5-METHOXYBENZONITRILE synthesis

11synthesis methods

Product Name:2-BROMO-5-METHOXYBENZONITRILE
CAS Number:138642-47-4
Molecular formula:C8H6BrNO
Molecular Weight:212.04

1527-89-5
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138642-47-4
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$7.00/250mg

Yield:138642-47-4 83%

Reaction Conditions:

with N-Bromosuccinimide;iodine in acetonitrile; for 12 h;Darkness;

Steps:

4.3. General procedure for the I2-catalyzed aromatic bromination of aryl ethers with NBS

General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH₃CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na₂S₂O₃ (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na₂SO₄ and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

References:

Pramanick, Pranab Kumar;Hou, Zhen-Lin;Yao, Bo [Tetrahedron,2017,vol. 73,# 50,p. 7105 - 7114]