Hexachloroethane → HCID 67350192, compound

HRID 1672559Notes

Reaction equation

HRID 1672559 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:27]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:27][C:4]1[O:5][C:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:9][N:8]=2)=[C:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 66696640HCID 66696640, compound

Product 1

HCID 67350192HCID 67350192, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 34D (3.37 g, 14.8 mmol) in THF (50 mL) was cooled to −78° C., followed by addition of LiHMDS (1M in THF, 16.3 ml, 16.3 mmol). After 0.5 hr at −78° C., hexachloroethane (3.50 g, 14.8 mmol) was added in one portion. The reaction was allowed to stir overnight with gradual warming to room temperature. The reaction was quenched with water and extracted with EtOAc. The combined organic extract was washed with water and brine, and then filtered through celite filter aid. The filtrate was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in minimal toluene and place on silica gel (Analogix® 25×115 column) and eluted with 2 column lengths of hexanes, then 5% to 50% EtOAc/hexanes. The result was 2.20 g (57%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.88 (m, 1H), 8.00-7.93 (m, 1H), 7.72-7.66 (m, 1H), 2.63 (s, 3H). MS (DCI+) m/z 263 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. extractionThe combined organic extract
  4. washwas washed with water and brine
  5. filtrationfiltered through celite
  6. filtrationfilter aid
  7. dry with materialThe filtrate was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in minimal toluene
  11. washplace on silica gel (Analogix® 25×115 column) and eluted with 2 column lengths of hexanes

Sources & evidence

ORD record
ord-a2ca443eab1348809060b0e303824199
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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