Toluene → HCID 3358921, Verbindung

Mix 3-bromobenzo[b]thiophene (5.83 g, 27.4 mmol), tetrakis(triphenylphosphine)palladium (O) (1.00 g, 0.865 mmol) and toluene (60 mL) and purge with nitrogen. Rapidly, add a 2 M aqueous solution of sodium carbonate (27 mL) and purge with nitrogen. Add a solution of 4-methoxyphenylboronic acid (4.57 g, 30.1 mmol) in methanol (13 mL), purge with nitrogen and heat at a gentle reflux for 4.5 hours. Let cool and stir at room temperature, overnight. TLC (30% dicloromethane in heptane) shows that all starting material is consumed. Dilute reaction mixture with ethyl acetate (100 mL). Wash with 2 M sodium carbonate (75 mL), water (75 mL), saturated sodium chloride (75 mL), dry (MgSO4) and concentrate (in vacuo) to give a residue. Purify the residue by column (silica) chromatography (20% dichloromethane in heptane) to give a mixture as a residue. Dissolve the residue in 30% ether in heptane, filter, evaporate and dry (0.5 mm Hg, room temperature) to give the title compound as a clear oil (5.47 g, 83% Yield).

1. custompurge with nitrogen
2. additionRapidly, add a 2 M aqueous solution of sodium carbonate (27 mL)
3. custompurge with nitrogen
4. custompurge with nitrogen
5. temperatureheat at
6. temperaturea gentle reflux for 4.5 hours
7. temperatureLet cool
8. customis consumed
9. additionDilute
10. customreaction mixture with ethyl acetate (100 mL)
11. washWash with 2 M sodium carbonate (75 mL), water (75 mL), saturated sodium chloride (75 mL)
12. dry with materialdry (MgSO4)
13. concentrationconcentrate (in vacuo)
14. customto give a residue
15. customPurify the residue by column (silica) chromatography (20% dichloromethane in heptane)
16. customto give a mixture as a residue
17. filtrationfilter
18. customevaporate
19. customdry (0.5 mm Hg, room temperature)

ORD-Eintrag

ord-feac39420d9b4def9e113e1257339100

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07253165B2