1-Bromo-3-chloropropane → HCID 59651987, compound

HRID 2042598Notes

Reaction equation

HRID 2042598 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]([CH3:17])([CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[CH3:2].Br[CH2:20][CH2:21][CH2:22][Cl:23].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]([CH3:17])([CH3:16])[C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:20][CH2:21][CH2:22][Cl:23])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 59651940HCID 59651940, compound

Product 1

HCID 59651987HCID 59651987, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from step 2 (1.0 g, 4.2 mmol), 1-bromo-3-chloropropane (1.0 g, 8 mmol) and K2CO3 in acetonitrile (20 mL) was heated to reflux for 24 h. The reaction was cooled, filtered, concentrated to an oil and purified by ISCO silica gel chromatography (10% EtOAc/hexanes) to give 0.7 g.

Workup

  1. temperatureto reflux for 24 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. custompurified by ISCO silica gel chromatography (10% EtOAc/hexanes)
  6. customto give 0.7 g

Sources & evidence

ORD record
ord-915f7ebe51fe4c61bbb470855432f216
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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