Tetrabutylammonium Fluoride Trihydrate → 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-methyl-3,4-dihydro-2H-pyrrole

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (Example I14) (1.83 g) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (see WO 2007125984) (1.38 g) in THF (25 ml) was added at −5° C. tetrabutylammonium fluoride trihydrate (TBAF) (0.41 g) dissolved in THF (15 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture concentrated and the residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:6) to give 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-methyl-3,4-dihydro-2H-pyrrole (2.50 g). 1H-NMR (400 MHz, CDCl3): 7.95-7.25 (m, 6H), 4.88 (d, 1H), 4.42 (d, 1H), 3.75 (d, 1H), 3.40 (d, 1H) ppm.

1. customwas added at −5° C.
2. concentrationThe reaction mixture concentrated
3. customthe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:6)

ORD 기록

ord-0afb244090c744bd8ce0752813c79262

출처 데이터셋

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08946447B2