Hexachloroethane → HCID 90087216, compound

HRID 2276734Notes

Reaction equation

HRID 2276734 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl.C(O)(C(F)(F)F)=O>C(OCC)C.O.CC#N>[Cl:26][C:13]1[C:8]([NH:7][C:6](=[O:20])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[C:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 6422Trifluoroacetic acidHCID 13926238HCID 13926238, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 90087216HCID 90087216, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of tert-butyl[1,1′-biphenyl]-2-ylcarbamate (synthesized according to Tsang et al., J. Org. Chem., 7603 (2008)) (12.5 g, 46.4 mmol) in diethyl ether (125 mL) at −30° C. was added tert-butyllithium (1.6 M in pentane, 174 mL, 278 mmol) slowly over 15 minutes. The reaction mixture was stirred for 6 h, then a solution of perchloroethane (43.9 g, 186 mmol) in diethyl ether (125 mL) was added over 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride and extracted twice with EtOAc. The organic layers were washed with brine, dried with sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (EtOAc/petroleum ether) to give Preparation 8A (8.5 g, 60%). HPLC: RT=2.432 min (H2O/MeCN with TFA, SunFire C18 3.5 μm, 4.6×150 mm, gradient=30 min, wavelength=220 and 254 nm).

Workup

  1. stirringstirred overnight
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. extractionextracted twice with EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (EtOAc/petroleum ether)
  8. customto give

Sources & evidence

ORD record
ord-bedafe49e40543eb88471ead39fbb7ef
Source dataset
uspto-grants-2015_09
Patent number
US09133126B2

Reaction notes

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