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ChemicalBook CAS DataBase List 4-METHOXYPHENYL ISOCYANIDE

4-METHOXYPHENYL ISOCYANIDE synthesis

5synthesis methods
To an ice-cooled flask containing a solution of 10.5 gm (0.065 mole) of p-methoxyformanilide in 37.1 gm (0.47 mole) of pyridine and 13.0 ml (0.16 mole) of chloroform is added dropwise at 0°C 6.12 gm (0.040 mole) of phosphorus oxychloride. The solution is stirred for 1? hr at room temperature and then added to 55 ml of ice-water. The water layer is extracted with two 10-ml portions of chloroform; the combined chloroform layer is dried and distilled under reduced pressure, to afford 3.5 gm (40%), b.p. 767C (1.0 mm Hg), IR 2137 c m " 1 (R—NC).
Preparation of p-Methoxyphenyl Isonitrile
-

Yield: 68%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 100; for 12 h;Inert atmosphere;

Steps:

13
Put sodium difluorochloroacetate 1 (0.2mmol, 31mg), K2CO3 (0.2mmol, 28mg) and p-anisidine (2a, 0.1mmol, 12.3mg) into a 25mL reaction tube, evacuated and filled with nitrogen (three times ). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours. After cooling to room temperature, filter and add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, and then take the organic layer and add a small amount of silica gel to spin dry column chromatography. Yellow solid product 3a (70% yield).

References:

CN112279789, 2021, A Location in patent:Paragraph 0033; 0088-0089

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