반응 #441259

반응 방정식

6-Methoxy -benzo[b]thiophene

n-butyllithium

iodobenzene

lithium chloride

triflate

iodobenzene

→

title compound

수율 68.4%

6-Methoxy-2-phenyl-benzo[b]thiophene

수율 68.4%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.WAITand at room temperature for 0.5 hrs
2. 2
   workup.STIRRINGThe reaction was then stirred at room temperature for 15 minutes
3. 3
   workup.STIRRINGthe reaction stirred at room temperature for 3 hrs
4. 4
   workup.ADDITIONmust be added
5. 5
   기타The reaction
6. 6
   온도can be refluxed overnight
7. 7
   기타The solvent was evaporated
8. 8
   추출extracted into ethyl acetate
9. 9
   건조The combined organic layers was dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated
12. 12
    기타The crude product was chromatographed on silica gel using 100% Hexanes to 1% ethyl acetate/hexanes as the gradient eluant

실험 절차

To a solution of 6-Methoxy -benzo[b]thiophene (250 mg, 1.52 mmol) in 3.7 mL THF at −20° C. was added dropwise n-butyllithium (0.67 mL, 1.67 mmol). The mixture was stirred at 0° C. for 1.5 hrs. and at room temperature for 0.5 hrs. Anhydrous zinc chloride (269 mg, 1.97 mmol) in 1.9 mL of THF was added by cannula to the reaction. The reaction was then stirred at room temperature for 15 minutes and then Pd(Ph3P)4 (70 mg, 0.06 mmol) and iodobenzene (0.22 mL, 1.97 mmol) were added and the reaction stirred at room temperature for 3 hrs. Other aromatic or heteroaromatic bromides, iodides or triflates can replace iodobenzene in this procedure. If a triflate is used 3 equivalents of anhydrous lithium chloride must be added. The reaction can be refluxed overnight to push it towards completion. The solvent was evaporated and the residue was diluted water and extracted into ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using 100% Hexanes to 1% ethyl acetate/hexanes as the gradient eluant to yield 250 mg of the title compound.

출처