5-Ethynyl-2-methoxybenzonitrile synthesis

Yield:1062617-60-0 69%

Reaction Conditions:

with caesium carbonate in dichloromethane; for 2 h;

Steps:

16.2 Step 2) 5-Ethynyl-2-methoxy-benzonitrile

Step 2) 5-Ethynyl-2-methoxy-benzonitrile To a stirred solution of 2-Fluoro-5-trimethylsilanylethynyl-benzonitrile (0.935 g, 4.3 mmol), in dry methylene chloride (10 mL) and methanol (10 mL) was added cesium carbonate (1.7 g, 5.2 mmol) and stirred for 2 h under a nitrogen atmosphere. The mixture was diluted with diethyl ether (100 mL), and partitioned between diethyl ether and H₂O (100 mL), and the aqueous layer was extracted with diethyl ether (50 mL), washed with brine and dried over MgSO₄, filtered and concentrated in vacuo. Purification by flash chromatography (20-30% ethyl acetate/petroleum ether) gave the title compound as a tan solid (0.468 g, 69%), identified by NMR and mass spectral analyses. Mp: 100-101° C. MS (EI+): 157 (M+).

References:

US2009/48320,2009,A1 Location in patent:Page/Page column 35