Hexachloroethane → HCID 66696662, compound

HRID 1672591Notes

Reaction equation

HRID 1672591 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:11][C:12]([F:27])([F:26])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][CH:22]=[N:21][C:20]=2[C:24]#[N:25])=[CH:15][CH:14]=1.[Cl:28]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.O>[Cl:28][C:22]1[O:23][C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:12]([F:11])([F:26])[F:27])=[CH:18][CH:17]=2)=[C:20]([C:24]#[N:25])[N:21]=1

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 2739747HCID 2739747, compound

Product 1

HCID 66696662HCID 66696662, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (1.0 M in THF, 4.5 mL, 4.5 mmol) was added dropwise to a solution of Example 56C (0.980 g, 4.11 mmol) in THF (13 mL) at −78° C. After 30 min solid hexachloroethane (0.974 g, 4.11 mmol) was added in one portion. The reaction was allowed to warm to room temperature while stirring overnight during which a solid formed. The mixture was diluted with hexanes and water, and filtered. The filtrate was diluted with EtOAc, and the phases separated. The organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was dissolved in toluene, loaded on silica gel, and eluted with 1 column length of hexanes and then 0% to 30% EtOAc:hexanes to afford 0.51 g (46%) of the title compound as a yellow milky oil. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=8.2, 2H), 7.81 (d, J=8.3, 2H).

Workup

  1. customformed
  2. filtrationfiltered
  3. additionThe filtrate was diluted with EtOAc
  4. customthe phases separated
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude product was dissolved in toluene
  10. washeluted with 1 column length of hexanes

Sources & evidence

ORD record
ord-3828dd16e91c411b9b12c2acdfe11d6c
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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