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2-Bromomethyl-4-methoxy-benzonitrile synthesis

2synthesis methods
21883-13-6 Synthesis
4-METHOXY-2-METHYLBENZONITRILE

21883-13-6
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$9.00/1g

2-Bromomethyl-4-methoxy-benzonitrile

28970-91-4
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Yield:28970-91-4 81%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 80; for 16 h;

Steps:

269 2-(bromomethyl)-4-methoxybenzonitrile

2-(bromomethyl)-4-methoxybenzonitrile
Into a 50-mL round-bottom flask, was placed a mixture of 4-methoxy-2-methylbenzonitrile (2 g, 13.59 mmol, 1.00 equiv), CCl4 (30 mL), NBS (2.67 g, 15.00 mmol, 1.10 equiv) and BPO (100 mg, 0.39 mmol, 0.03 equiv). The resulted solution was stirred for 16 h at 80° C. After the reaction, it cooled to rt. The reaction mixture was washed with 3×20 mL of water. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 2.50 g (81%) of 2-(bromomethyl)-4-methoxybenzonitrile as a yellow solid. LC-MS (ESI) m/z: calculated for C9H8BrNO: 224. found: 395 [M+H]+. Rt: 1.44 min.

References:

US2015/315198,2015,A1 Location in patent:Paragraph 0786; 0787