Reacción #1960519

Ecuación de reacción

2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester

pyridine

bromoacetyl chloride

→

2-[6-(2-bromo-acetoxy)-naphthalen-2-yl]-propionic acid methyl ester

Rendimiento 45.9%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate
2. 2
   Secadoby drying over sodium sulphate and distillation
3. 3
   Otroto get crude compound, which
4. 4
   Otrowas purified by column chromatography

Procedimiento

To a solution of 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester (20 grams) and pyridine (10.3 grams) in dichloromethane (200 ml) maintained at 0-5° C. under N2 atmosphere was added dropwise bromoacetyl chloride (19.6 grams). The reaction was stirred at the same temperature for one hour. The reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate followed by drying over sodium sulphate and distillation to get crude compound, which was purified by column chromatography using hexane as eluant to get pure 2-[6-(2-bromo-acetoxy)-naphthalen-2-yl]-propionic acid methyl ester (14 grams) as a dark brown syrup. The pure product was characterized using 1H NMR spectroscopy in CDCl3 δ 1.55 (d, 3H, CH3), 3.65 (s, 3H, Ester), 3.82 (q, 1H, CH), 4.08 (s, 2H, OCH2) 7.20 (dd, 1H, Ar), 7.4 (dd, 1H, Ar), 7.57 (d, 1H, Ar), 7.72 (d, 1H, Ar), 7.78 (d, 1H, Ar), 7.84 (d, 1H, Ar).

Fuente