Hexachloroethane → HCID 66696597, compound

HRID 1672553Notes

Reaction equation

HRID 1672553 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[O:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOCC>[Cl:26][C:4]1[O:5][C:6]([C:7]2[O:8][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:10][CH:11]=2)=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 66696609HCID 66696609, compound

Product 1

HCID 66696597HCID 66696597, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 31A (0.62 g, 2.8 mmol) in THF (20 mL) at −78° C. was added LiHMDS (1 M in THF, 3.4 mL, 3.4 mmol) dropwise over a period of 6-8 min. After 30 min hexachloroethane (1.35 g, 5.68 mmol) was added at once as a solid and the mixture was left to stir overnight warming to ambient temperature. The mixture was diluted with Et2O and washed with aqueous NH4Cl solution and water. The organic layer was separated and concentrated in vacuo, and the residue chromatographed on silica gel with EtOAc/hexanes (0%-20%) to yield 0.6 g (84%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.46 (m, 1H), 7.04 (d, J=3.4, 1H), 2.33 (s, 3H).

Workup

  1. waitthe mixture was left
  2. washwashed with aqueous NH4Cl solution and water
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on silica gel with EtOAc/hexanes (0%-20%)

Sources & evidence

ORD record
ord-1c1e3ce264f04c26b1baac47f1c8059f
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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