반응 #168951

반응 방정식

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

cyclopropylmagnesium bromide

hydrochloric acid

→

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

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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%).

출처