Carbon Tetrachloride → HCID 86674593, compound

HRID 2170705Notes

Reaction equation

HRID 2170705 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C@@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH:2]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>CCOC(C)=O>[Br:22][CH2:14][C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[O:7][C@@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 51924568HCID 51924568, compound

Product 1

HCID 86674593HCID 86674593, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a 250 mL round-bottom flask was (S)-methyl 2-(m-tolyloxy)propanoate (2.0 g, 10.3 mmol, 1 equiv), NBS (1.83 g, 10.3 mmol, 1 equiv), AIBN (169 mg, 1.03 mmol, 0.1 equiv) and CCl4 (100 mL). The reaction mixture was refluxed for 16 h at 80° C. The completion of the reaction was monitored by analytical HPLC. The reaction mixture was allowed to cool to room temperature. The crude mixture was dissolved in AcOEt (100 mL) and washed with a 0.5N HCl aqueous solution (×2), a saturated NaHCO3 solution (×2) and brine, dried over Na2SO4. The filtrate was concentrated to obtain the crude product which was purified by flash chromatography (AcOEt/Hexane 0->60%) to obtain the title compound.

Workup

  1. customTo a 250 mL round-bottom flask was
  2. temperatureto cool to room temperature
  3. washwashed with a 0.5N HCl aqueous solution (×2)
  4. dry with materiala saturated NaHCO3 solution (×2) and brine, dried over Na2SO4
  5. concentrationThe filtrate was concentrated
  6. customto obtain the crude product which
  7. customwas purified by flash chromatography (AcOEt/Hexane 0->60%)

Sources & evidence

ORD record
ord-ce6db416fa9b42e2b097072a486f4daa
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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