Benzyl Bromide → Ethyl 1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Temperatur

80 °C

Benzyl bromide (10.9 mL, 91.66 mmol) was added to the solution of crude ethyl 3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (25 g, 83.33 mmol) and K2CO3 (23.03 g, 166.66 mmol) in acetonitrile. The reaction mixture was stirred for 13 h at 80° C. Then the reaction mixture was cooled to RT and then diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×400 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was then purified by column chromatography (100-200 mesh Silica gel; 10% ethyl acetate/hexane; Rf-value 0.8) to afford title compound (29 g, 89.18% yield, pale yellow color oil).

1. temperatureThen the reaction mixture was cooled to RT
2. extractionThe aqueous layer was extracted with EtOAc (2×400 mL)
3. dry with materialCombined organic layer was dried over anhydrous Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto yield crude mass which
6. customwas then purified by column chromatography (100-200 mesh Silica gel; 10% ethyl acetate/hexane; Rf-value 0.8)

ORD-Eintrag

ord-8b724a8843334160a54ac07f9bcc9f9f

Quelldatensatz

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09302988B2