Réaction #1960519

Équation de réaction

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

Rendement 45.9%

Solvants

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source