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ChemicalBook CAS DataBase List 5-Cyano-2-methoxybenzaldehyde
21962-53-8

5-Cyano-2-methoxybenzaldehyde synthesis

4synthesis methods
-

Yield: 88%

Reaction Conditions:

with sodium methylate at 20;

Steps:

38.1 Step 1: 5-cyano-2-methoxybenzaldehyde (38a).
To a solution of 5-cyano-2-fluorobenzaldehyde (500 mg, 3.35 mmol) in MeOH (5 mL) was added CH3ONa (362 mg, 6.71 mmol, 2 equiv). The mixture was stirred at rt for 3 h. After the reaction was completed, the product was extracted with EtOAc (20 mL x 3). The organic layers were combined, washed with saturated brine, dried over Na2SO4 and filtered. All volatiles were evaporated in vacuo and the product was obtained after flash chromatography (hexane: EtOAc = 30: 1) as a white solid (478 mg, 88%), 1H NMR (400 MHz, Chloroform-d) δ 10.44 (s, 1H), 8.13 (s, 1H), 7.84 (d, J = 8.8 Hz, 1H), 7.12 (d, J = 8.9 Hz, 1H), 4.04 (s, 3H).

References:

Qiu, Yangyi;Chan, Shu Ting;Lin, Lin;Shek, Tsun Lam;Tsang, Tsz Fung;Barua, Nilakshi;Zhang, Yufeng;Ip, Margaret;Chan, Paul Kay-sheung;Blanchard, Nicolas;Hanquet, Gilles;Zuo, Zhong;Yang, Xiao;Ma, Cong [European Journal of Medicinal Chemistry,2019,vol. 178,p. 214 - 231]