Reaction #1960519

Reaction equation

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

Yield 45.9%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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