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

温度

-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レコード

ord-54535bf4a30949a990e50a5e58abae5a

出典データセット

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07109354B2