Hexachloroethane → HCID 66696688, compound

HRID 1672535Notes

Reaction equation

HRID 1672535 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][C:12]1[N:13]=[CH:14][O:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1.[Cl:27]C(Cl)(Cl)C(Cl)(Cl)Cl>O1CCCC1>[Cl:27][C:14]1[O:15][C:16]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)=[C:12]([CH3:11])[N:13]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 60070918HCID 60070918, compound

Product 1

HCID 66696688HCID 66696688, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 19.4 mL, 19.4 mmol) was added dropwise to a solution of Example 12A (4.0 g, 17.6 mmol) in tetrahydrofuran (80 mL) at −78° C. After stirring 30 min, solid hexachloroethane (8.34 g, 35.2 mmol) was added in one portion, and the reaction was allowed to gradually warm to ambient temperature. After 16 hours the reaction was quenched with half-saturated NH4Cl solution. The product was extracted with diethyl ether, and the combined organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix Intelliflash 280; 0% to 25% ethyl acetate/hexanes; SF65-600 g column; loading with hexane/CH2Cl2) to yield 4.69 g of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.87 (m, 2H), 7.82 (m, 2H), 2.40 (s, 3H). MS (DCI+) m/z 262 (M+H)+.

Workup

  1. customAfter 16 hours the reaction was quenched with half-saturated NH4Cl solution
  2. extractionThe product was extracted with diethyl ether
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (Analogix Intelliflash 280; 0% to 25% ethyl acetate/hexanes; SF65-600 g column; loading with hexane/CH2Cl2)

Sources & evidence

ORD record
ord-28e8c07bc3ed4db2a8bd354a14f1bbc8
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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