Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 71144442, compound

Temperature

-78 °C

A 250 mL round-bottomed flask containing magnesium turnings (0.685 g, 28.2 mmol) and Et2O (25 mL) was added diisobutylaluminum hydride 1.0 M solution in hexanes (0.18 mL, 0.180 mmol) followed by dropwise addition of 4-bromobenzotrifluoride (2.0 mL, 14.28 mmol). The solution was stirred for 1.5 hours during which it turned from turbid to dark brown in color. The reaction mixture was cooled to −78° C. in a dry ice/acetone bath and then a solution of (S,E)-2-methyl-N-((3-methylpyridin-2-yl)methylene)propane-2-sulfinamide (2.15 g, 7.67 mmol) in THF (15 mL) was added dropwise over 5 minutes. The reaction was stirred for 5 hours during which it warmed to rt. The reaction was quenched with saturated aqueous NH4Cl (50 mL) and H2O (25 mL). The reaction mixture was extracted with EtOAc (2×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to yield the initial product which was purified by silica gel flash column chromatography (using a 80G ISCO cartridge) and eluted using hexanes/EtOAc gradient to yield the desired product

1. stirringThe reaction was stirred for 5 hours during which it
2. temperaturewarmed to rt
3. customThe reaction was quenched with saturated aqueous NH4Cl (50 mL) and H2O (25 mL)
4. extractionThe reaction mixture was extracted with EtOAc (2×100 mL)
5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
6. concentrationconcentrated

ORD record

ord-f5c9fd1f89314ed996db1ec1e9aa0515

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096527B2