Hexachloroethane → HCID 66696628, compound
Reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][O:12][CH:13]([O:29][CH3:30])[C:14]1[N:15]=[CH:16][O:17][C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.[Cl:31]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:31][C:16]1[O:17][C:18]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=2)=[C:14]([CH:13]([O:12][CH3:11])[O:29][CH3:30])[N:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
LiHMDS (1.0 M in THF, 5.4 mL, 5.4 mmol) was added slowly to a solution of Example 52C (1.42 g, 4.94 mmol) in THF (20 mL) at −78° C. After 30 min solid hexachloroethane (1.29 g, 5.44 mmol) was added in one portion, and the reaction mixture was allowed to proceed for 5.5 hr with gradual warming to 5° C. The reaction was quenched with saturated aq NH4Cl solution (10 mL), and the mixture was partitioned between H2O and Et2O. The aqueous phase was extracted once with Et2O, and the combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The result was 1.83 g (115%) of the title compound as a dark yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 7.94 (d, J=8.5, 2H), 7.88 (d, J=8.8, 2H), 5.53 (s, 1H), 3.33 (s, 6H). MS (DCI+) m/z 339 (M+NH4).
Workup
- customThe reaction was quenched with saturated aq NH4Cl solution (10 mL)
- customthe mixture was partitioned between H2O and Et2O
- extractionThe aqueous phase was extracted once with Et2O
- extractionthe combined organic extract
- washwas washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3a7d33b2a6a84476b234ad3620d4cff2
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998993B2
Reaction notes
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