3-Bromodiphenyl ether → 5-(3-phenoxy-phenyl)-3,4-dihydro-2H-pyrrole

To a cold solution (−78° C.) of 1-bromo-3-phenoxy-benzene (10.13 g, 40.6 mmol) in anhydrous THF (100 mL) and under nitrogen is added n-BuLi (1.6M, 44.7 mmol, 27 mL). The mixture is allowed to stir for 30 minutes before being added to a cold solution (−78° C.) of 1-(tert-Butoxycarbonyl)-2-pyrrolidinone in anhydrous THF (50 mL) under nitrogen via cannula. The resulting mixture is allowed to warm to room temperature overnight before being quenched with water (200 mL) and extracted with EtOAc (3×100 mL). The organics were collected, dried over Na2SO4, filtered and concentrated under reduced pressures. The residue is dissolved in CH2Cl2 (20 mL) and TFA (10 mL) is added with stirring. The mixture is stirred for 30 minutes and quenched over ice cold sat. NaHCO3, extracted with CH2Cl2 (3×100 mL) and the organics were combined, dried over Na2SO4, filtered and concentrated under reduced pressures. The residue is purified by silica gel column chromatography (20% EtOAc/Hexanes) to give 5-(3-phenoxy-phenyl)-3,4-dihydro-2H-pyrrole as light yellow oil (6.1 g, 63%). LCMS m/z 238 (M+1).

1. custombefore being quenched with water (200 mL)
2. extractionextracted with EtOAc (3×100 mL)
3. customThe organics were collected
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressures
7. dissolutionThe residue is dissolved in CH2Cl2 (20 mL)
8. additionTFA (10 mL) is added
9. stirringwith stirring
10. stirringThe mixture is stirred for 30 minutes
11. customquenched over ice cold sat. NaHCO3
12. extractionextracted with CH2Cl2 (3×100 mL)
13. dry with materialdried over Na2SO4
14. filtrationfiltered
15. concentrationconcentrated under reduced pressures
16. customThe residue is purified by silica gel column chromatography (20% EtOAc/Hexanes)

ORDレコード

ord-433893680e7144db9128dc8c6fccf424

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08207183B2