Hexachloroethane → HCID 66696664, compound

Temperature

-78 °C

LiHMDS (1.0 M in THF, 24 mL, 24 mmol) was added to a solution of Example 54A (4.90 g, 21.9 mmol) in THF (73 mL) at −78° C. The reaction was stirred at −78° C. for 30 min, and then solid hexachloroethane (5.20 g, 21.9 mmol) was added in one portion. The reaction was allowed to stir overnight while warming to room temperature. The reaction was quenched with water and the product extracted with EtOAc. The combined organic extract was washed with water and brine, and filtered through celite. The filtrate was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was dissolved in toluene and loaded on silica gel (Analogix® 25×115 column), and eluted with 2 column lengths of hexanes then 5% to 50% EtOAc/hexanes. The result was 4.1 g (73%) of the title compound as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.63 (d, J=8.5, 2H), 7.58 (d, J=8.7, 2H), 6.68 (t, J=56.5, 1H), 2.77 (q, J=7.5, 2H), 1.31 (t, J=7.5, 3H). MS (DCI+) m/z 258 (M+H).

1. stirringto stir overnight
2. temperaturewhile warming to room temperature
3. customThe reaction was quenched with water
4. extractionthe product extracted with EtOAc
5. extractionThe combined organic extract
6. washwas washed with water and brine
7. filtrationfiltered through celite
8. dry with materialThe filtrate was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. dissolutionThe crude product was dissolved in toluene
12. washeluted with 2 column lengths of hexanes

ORD record

ord-026d799ade844b4ba940d757efa4e55e

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998993B2