반응 #420030

반응 방정식

trimethylacetic acid

6-methoxybenzo[b]thiophene

1-bromo-4-fluorobenzene

potassium carbonate

→

2-(4-fluorophenyl)-6-methoxybenzo[b]thiophene

수율 54.1%

용매

DMA

반응 조건

후처리

1. 1
   기타The microwave vial was sealed
2. 2
   기타purged with nitrogen
3. 3
   기타irradiation at 150° C. for 2 h
4. 4
   workup.ADDITIONUpon completion the reaction mixture was diluted with water
5. 5
   추출extracted with EtOAc
6. 6
   세척The combined organic layers were then washed with brine
7. 7
   건조dried over anhydrous MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo
10. 10
    기타The resulting crude material was purified via trituration 2× with heptane
11. 11
    기타the remaining triturate (
12. 12
    workup.ADDITIONcontaining some product)
13. 13
    농축was concentrated
14. 14
    기타purified by column chromatography (SiO2, 0-30% EtOAc/Heptane)

실험 절차

To a 5 mL microwave vial was added a solution of 6-methoxybenzo[b]thiophene (400 mg, 2.44 mmol) in anhydrous DMA (3 mL) followed by 1-bromo-4-fluorobenzene (448 mg, 2.56 mmol), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (BrettPhos palladacycle 1st generation, 97 mg, 0.12 mmol), trimethylacetic acid (746 mg, 7.31 mmol) and potassium carbonate (1.01 g, 7.31 mmol). The microwave vial was sealed, purged with nitrogen and subjected to microwave irradiation at 150° C. for 2 h. Upon completion the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were then washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting crude material was purified via trituration 2× with heptane and the remaining triturate (containing some product) was concentrated and purified by column chromatography (SiO2, 0-30% EtOAc/Heptane) to afford 2-(4-fluorophenyl)-6-methoxybenzo[b]thiophene (340 mg, 1.32 mmol, 54% yield). 1H NMR (400 MHz, (CD3)2SO) δ ppm=3.79-3.93 (m, 3H), 7.01 (dd, J=8.59, 2.53 Hz, 1H), 7.24-7.42 (m, 2H), 7.56 (d, J=2.53 Hz, 1H), 7.67-7.86 (m, 4H). LC/MS (m/z, MH+): 258.8.

출처