Reaktion #168951

Reaktionsgleichung

4-bromo-1-chloro-2-methoxy-benzene

cyclopropylmagnesium bromide

hydrochloric acid

→

1-chloro-4-cyclopropyl-2-methoxy-benzene

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 65° C. for 48 hours
2. 2
   Temperaturthe mixture was then cooled to room temperature
3. 3
   workup.STIRRINGstirred for 30 minutes
4. 4
   SonstigeThe reaction mixture was partitioned between ethyl acetate and water
5. 5
   WaschenThe combined organic phase was washed with brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel chromatography (2% ethyl acetate in hexane)

Vorschrift

To a solution of 4-bromo-1-chloro-2-methoxy-benzene (1.45 g, 6.55 mmol) in dry tetrahydrofuran (10 ml), was added {1,3-bis(diphenylphosphino)-propane}dichloronickel (II) and cyclopropylmagnesium bromide (46 ml, 0.5 M in tetrahydrofuran, 23 mmols) at room temperature. The solution was stirred at room temperature for 2 hours, and then heated at 65° C. for 48 hours. Aqueous hydrochloric acid solution (1 N, 20 mL) was added, and the mixture was then cooled to room temperature and stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (2% ethyl acetate in hexane) to yield 1-chloro-4-cyclopropyl-2-methoxy-benzene as yellow oily residue (0.81 g, 67%).

Quelle