Reaktion #47338

Reaktionsgleichung

3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester

N-bromosuccinimide

→

4-bromo-3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester

Ausbeute 71.1%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwas washed with water (1×50 mL)
2. 2
   Trocknena saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Waschenrinsed with dichloromethane
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes)

Vorschrift

A solution of 3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (0.69 g, 2.65 mmol) in dichloromethane (14 mL) was treated with N-bromosuccinimide (0.50 g, 2.80 mmol) and 2,2′-azobis(2,4-dimethylvaleronitrile) (31.6 mg, 0.12 mmol). The reaction was then warmed to 45° C. where it stirred overnight. At this time, the reaction was diluted with dichloromethane (50 mL) and was washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate, filtered, rinsed with dichloromethane, and concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes) afforded impure 4-bromo-3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (638.8 mg, 71%) as a yellow oil. The material was used without further purification.

Quelle