Hydrochloric Acid → 3'-Bromo-2,2,2-trifluoroacetophenone

Temperatur

-78 °C

In a dry round bottom flask, 3-bromo-benzoic acid methyl ester (2 g, 9.3 mmol, Aldrich Chemical Company) and trimethyl(trifluoromethyl)silane (1.72 mL, 11.6 mmol, Aldrich Chemical Company) were dissolved in dry toluene (50 mL). Upon cooling the solution to −78° C., TBAF (232 μL, 0.23 mmol) was added and the reaction was allowed to warm up slowly to rt overnight. After stirring for 20 hr, 2N HCl (50 mL) and EtOAc (100 mL) were added, the layers were separated, and the aqueous layer was extracted with another portion of EtOAc. The combined organic fractions were dried (MgSO4), concentrated in vacuo, and resulting crude oil was purified using SiO2 flash chromatography (elution: 5–20% EtOAc in hexanes) to give 1.5 g (65%) the title compound as a light yellow oil. 1H-NMR (CDCl3; 400 MHz) δ 8.18 (br s, 1H), 7.98–8.00 (m, 1H), 7.82–7.85 (m, 1H), 7.42–7.46 (m, 1H). 19F-NMR (CDCl3; 400 MHz) δ −72.06 (s).

1. temperatureto warm up slowly to rt overnight
2. customthe layers were separated
3. extractionthe aqueous layer was extracted with another portion of EtOAc
4. dry with materialThe combined organic fractions were dried (MgSO4)
5. concentrationconcentrated in vacuo
6. customresulting crude oil
7. customwas purified
8. washSiO2 flash chromatography (elution: 5–20% EtOAc in hexanes)

ORD-Eintrag

ord-2b2cda64ac6944fca39ba598ad06d0d8

Quelldatensatz

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07138530B2