Boron trifluoride etherate → 1-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Temperatur

50 °C

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (1.0 g, 2.23 mmol) in 1:2 of 1,2-dichloroethane/MeCN (12 mL) was added Et3SiH (0.755 mL, 4.68 mmol) and BF3.OEt2 (0.34 mL, 2.90 mmol) simultaneously at 20° C. The reaction mixture was heated at 50° C. for 4 h and quenched by the addition of aq. NaHCO3 (10 mL). The volatiles were evaporated under reduced pressure; the resulting mixture was extracted with dichloromethane (2×20 mL), washed with brine (5 mL), dried over sodium sulfate, concentrated and was purified by silica gel column chromatography to furnish 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (0.60 g).

1. customquenched by the addition of aq. NaHCO3 (10 mL)
2. customThe volatiles were evaporated under reduced pressure
3. extractionthe resulting mixture was extracted with dichloromethane (2×20 mL)
4. washwashed with brine (5 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customwas purified by silica gel column chromatography

ORD-Eintrag

ord-78dba44cbf6f40d5a917c3fe420853e5

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08466114B2