Hexachloroethane → HCID 66696652, compound

HRID 1672549Notes

Reaction equation

HRID 1672549 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][CH:21]=[N:20][C:19]=2[CH3:23])=[CH:14][C:13]=1[F:24].[Cl:25]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOCC>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][C:21]([Cl:25])=[N:20][C:19]=2[CH3:23])=[CH:14][C:13]=1[F:24]

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 66696592HCID 66696592, compound

Product 1

HCID 66696652HCID 66696652, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (1 M in THF, 4.4 mL, 4.4 mmol) was added dropwise via syringe to a solution of Example 29A (1.03 g, 4.02 mmol) in THF (20 mL) at −78° C. After 30 min solid hexachloroethane (1.90 g, 8.04 mmol) was added in one portion and the reaction mixture was allowed to gradually warm to ambient temperature over 16 hr. The reaction was diluted with Et2O and quenched with half-saturated aqueous NH4Cl solution. The separated aqueous phase was extracted with Et2O, and the combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 0% to 15% EtOAc/hexanes eluant; SF25-120 g column) afforded 1.07 g (92%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.84 (dd, J=8.4, 7.4 1H), 7.57 (dd, J=9.9, 2.0 1H), 7.39 (dd, J=8.5, 2.0 1H), 2.36 (s, 3H). MS (DCI+) m/z 290/292 (M+H).

Workup

  1. customquenched with half-saturated aqueous NH4Cl solution
  2. extractionThe separated aqueous phase was extracted with Et2O
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd0dbe2a30a54dfca8b2c8c0eebeaddd
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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