Hexachloroethane → HCID 66696594, compound

Temperature

-78 °C

A solution of Example 57A (7.32 g, 30.6 mmol) in THF (150 mL) was cooled to −78° C., and treated carefully with LiHMDS (1 M in THF, 37 mL, 37 mmol). The mixture was stirred at −78° C. for 20 minutes, then was treated all at once with hexachloroethane (14.5 g, 61.2 mmol). The flask was removed from the cold bath, and the reaction mixture was stirred overnight at room temperature. After this time, the mixture was diluted with Et2O and washed with saturated NH4Cl solution and water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (100% hexane, then 0% to 20% EtOAc/hexane) to afford 7.44 g (89%) of the title compound as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.68 (d, J=2.4, 1H), 7.87 (dd, J=8.4, 2.4, 1H), 7.48 (dd, J=8.7, 0.7, 1H), 2.57 (s, 3H). MS (DCI+) m/z 273/275 (M+H).

1. customThe flask was removed from the cold bath
2. stirringthe reaction mixture was stirred overnight at room temperature
3. additionAfter this time, the mixture was diluted with Et2O
4. washwashed with saturated NH4Cl solution and water
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was chromatographed on silica gel (100% hexane

ORD record

ord-e3c5d4515b3a43d99eb57d038c921935

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998993B2