1-Bromo-3-chloropropane → HCID 57550258, compound

HRID 548638Notes

Reaction equation

HRID 548638 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14]([O:16][CH3:17])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][Cl:28]>CC(C)=O>[Cl:28][CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14]([O:16][CH3:17])=[O:15])[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate

Product 1

HCID 57550258HCID 57550258, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate a51 (3.48 g, 14.8 mmol, 1 eq), potassium carbonate (4 g, 29.6 mmol, 2 eq) and 1-bromo-3-chloropropane a2 (1.6 ml, 16.2 mmol, 1.1 eq) in acetone (80 ml) is stirred at reflux overnight. The mixture is concentrated under vacuum then the residue is dissolved in ethyl acetate, and washed with a saturated solution of aqueous sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate and concentrated under vacuum to give 2.3 g of methyl 1-[4-(3-chloropropoxy)phenyl]-5-oxopyrrolidine-3-carboxylate a53 as a yellow oil.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture is concentrated under vacuum
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with a saturated solution of aqueous sodium hydrogenocarbonate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e4e631b344784efa861f32017969f4c9
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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