Hexachloroethane → HCID 66696632, compound

HRID 1672578Notes

Reaction equation

HRID 1672578 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:11][C:12]1[CH:13]=[C:14]([C:22]2[O:26][CH:25]=[N:24][C:23]=2[CH3:27])[CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19].[Cl:28]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:28][C:25]1[O:26][C:22]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([F:19])([F:21])[F:20])=[C:12]([Cl:11])[CH:13]=2)=[C:23]([CH3:27])[N:24]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 66696682HCID 66696682, compound

Product 1

HCID 66696632HCID 66696632, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (1.0 M in THF, 13 ml, 13 mmol) was added slowly via syringe to a solution of Example 45B (3.04 g, 11.6 mmol) in THF (50 mL) at −78° C. The solution was stirred 45 min, and then solid hexachloroethane (4.13 g, 17.4 mmol) was added in one portion. The reaction was allowed to proceed for 12 hr with gradual warming to ambient temperature. The reaction was quenched with half-saturated aq NH4Cl solution, and the product was extracted with Et2O. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (Analogix® Intelliflash 280™; 0% to 20% EtOAc/hexanes eluant; SF40-150 g column) to afford 3.02 g (88%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.97 (d, J=8.4, 1H), 7.86 (s, 1H), 7.75 (d, J=8.3, 1H), 2.42 (s, 3H). MS (DCI+) m/z 296 (M+H).

Workup

  1. waitto proceed for 12 hr
  2. customThe reaction was quenched with half-saturated aq NH4Cl solution
  3. extractionthe product was extracted with Et2O
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography (Analogix® Intelliflash 280™

Sources & evidence

ORD record
ord-c1904bff80cf40b2873a9935b992bec5
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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