반응 #48067

반응 방정식

1,3-dibromo-5-chlorobenzene

cyclopropylmagnesium bromide

→

desired product

수율 64.0%

1-bromo-3-chloro-5-cyclopropylbenzene

수율 64.0%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도cooled to RT
3. 3
   기타quenched with sat. NH4Cl solution
4. 4
   추출extracted with pentane
5. 5
   세척washed with water and brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered through a short pad of silica gel

실험 절차

To a solution of 1,3-dibromo-5-chlorobenzene (500 mg, 1.85 mmol) in THF (1 ml) was added cyclopropylmagnesium bromide (3698 μl, 0.5M solution in THF, 1.85 mmol) in a sealed tube and the reaction mixture was degassed with argon for 5 min before tetrakis(triphenylphosphine)palladium (0) (107 mg, 0.09 mmol) was added. The resulting solution was heated to 70° C. overnight, cooled to RT and then quenched with sat. NH4Cl solution and extracted with pentane. The organic phases were combined, washed with water and brine, dried over MgSO4 and filtered through a short pad of silica gel to give the desired product (272 mg, 64%) which did not require further purification. 1H NMR (CDCl3, 300 MHz): 7.28 (aptt, J=2.0 Hz, 1H), 7.08 (aptt, J=1.5 Hz, 1H), 6.97 (aptt, J=1.5 Hz, 1H), 1.83 (m, 1H), 1.04-0.97 (m, 2H), 0.72-0.67 (m, 2H).

출처