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tert-butyl 3-cyanobenzoate synthesis

2synthesis methods
-

Yield: 82.1%

Reaction Conditions:

with pyridine;dmap in dichloromethane at 0 - 20; for 20 h;

Steps:

1.A.B
To a mixture of tert-butanol (3.50 g, 47.22 mmol), pyridine (3.72 g, 46.78 mmol) and cat. DMAP in methylene chloride (15 mL) is added dropwise 3-cyanobenzoyl chloride (6.81 g, 41.07 mmol) and pyridine (3 mL) in methylene chloride (10 mL) at 0 °C. The resulting mixture is stirred at room temperature for 20 h. The solvent is evaporated, and the residue is purified by flash chromatography (1:1 methylene EPO chloride/hexanes) to afford 3-cyano-benzoic acid tert-butyl ester (6.84 g, 82.1% yield) as white solid. 1H NMR (300 MHz, CDCl3): δ 8.24 (1H, s), 8.20 (1H, dd, J = 7.9, 1.2 Hz), 7.78 (1H, dd, J= 6.7, 1.1 Hz), 7.52 (1H, m), 1.58 (9H, s).

References:

PTC THERAPEUTICS, INC. WO2006/44505, 2006, A2 Location in patent:Page/Page column 82-83