반응 #9799

반응 방정식

9-bromoanthracene

bromophenol

→

Anthracene

용매

hexane

Et2O

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred
2. 2
   온도warmed to RT over 30 min
3. 3
   기타The volatiles were removed under N2
4. 4
   기타purge
5. 5
   workup.DISSOLUTIONthe residue was redissolved in 3:1 THF/NMP (11 mL)
6. 6
   온도the reaction was heated to 100° C. for 2 h
7. 7
   온도The reaction was cooled to RT
8. 8
   기타the THF was removed
9. 9
   workup.ADDITIONThe residue was diluted with CH2Cl2
10. 10
    세척washed with 1 M HCl
11. 11
    건조dried over Na2SO4
12. 12
    기타The crude material was purified by flash chromatography

실험 절차

A solution of 9-bromoanthracene (0.67 g, 2.6 mmol, 1.2 eq) in dry Et2O (13 mL) under N2 was cooled to −30° C. and nBuli (1.6 M in hexane, 1.6 mL, 2.6 mmol, 1.2 eq) was added dropwise. The solution was stirred for 20 min. at −30° C. followed by dropwise addition of ZnCl2 (0.50 M in THF, 5.2 mL, 2.6 mmol, 1.2 eq). The reaction was stirred and warmed to RT over 30 min. The volatiles were removed under N2 purge and the residue was redissolved in 3:1 THF/NMP (11 mL). The MOM-protected bromophenol (2.2 mmol, 1.0 eq) and Pd(PtBu3)2 (22 mg, 44 μmol, 4 mol %) were added and the reaction was heated to 100° C. for 2 h. The reaction was cooled to RT and the THF was removed. The residue was diluted with CH2Cl2, washed with 1 M HCl, and dried over Na2SO4. The crude material was purified by flash chromatography.

출처