Hydrochloric Acid → 2-Chloro-1-(2,4,6-trifluorophenyl)ethan-1-one

To a mechanically stirred solution of 1,3,5-trifluorobenzene (6.0 mL, 58 mmol) in dichloroethane (14.0 mL) was added gradually AlCl3 (15.5 g, 116 mmol) in a period of 15 min with caution. Violent bumping and HCl gas evolution was observed. The mixture was carefully heated to reflux, and chloroacetyl chloride (5.5 mL, 69 mmol) was added drop wisely in a period of 45 min. The reaction mixture was heated at reflux for additional 6.0 h. The solution was cooled, carefully poured onto an ice/water slush (200 mL) and the aqueous solution was extracted with ether (3×50 mL). The combined ethereal layers were washed with 10% aqueous HCl (2×30 mL), 1.0 N aqueous NaOH (3×30 mL), and brine (25 mL). The solution was dried over MgSO4 and concentrated under reduced pressure to give 2-chloro-1-(2,4,6-trifluorophenyl)ethanone (5.28 g) as yellow solids in 51% yield: 1H NMR (500 MHz, CDCl3) δ 6.79-6.76 (m, 2 H), 4.50 (s, 2 H).

1. temperatureThe mixture was carefully heated
2. temperatureto reflux
3. temperatureThe reaction mixture was heated
4. temperatureat reflux for additional 6.0 h
5. temperatureThe solution was cooled
6. extractionthe aqueous solution was extracted with ether (3×50 mL)
7. washThe combined ethereal layers were washed with 10% aqueous HCl (2×30 mL), 1.0 N aqueous NaOH (3×30 mL), and brine (25 mL)
8. dry with materialThe solution was dried over MgSO4
9. concentrationconcentrated under reduced pressure

ORDレコード

ord-ef459cc9ec6444a1bea4bc96e37710f6

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08946268B2