1,2-Dibromo-3-Chloropropane → 3-Chloromethyl-6-(2-(5-(3-chloro-phenyl)-2-oxo-3-oxazolidinyl)propyl)-1,4-benzodioxane

HRID 374888Notes

Reaction equation

HRID 374888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:24])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].Br[CH2:29][CH:30](Br)[CH2:31][Cl:32]>CO>[Cl:32][CH2:31][CH:30]1[CH2:29][O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH:14]([N:10]3[CH2:9][CH:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[O:12][C:11]3=[O:13])[CH3:24])=[CH:17][C:18]=2[O:23]1

Participants

5

Reactant 3

HCID 72801,2-Dibromo-3-ChloropropaneHCID 10942334Sodium MethoxideHCID 156692045-(3-Chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

Product 1

HCID 542652843-Chloromethyl-6-(2-(5-(3-chloro-phenyl)-2-oxo-3-oxazolidinyl)propyl)-1,4-benzodioxane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727, Example 1, is combined with two equivalents of 2N sodium methoxide in methyl alcohol and the resulting slurry is stirred at room temperature for 30 minutes. One equivalent of 1,2-dibromo-3-chloropropane is added and the stirring is continued at room temperature for 24 hours. The solvent is evaporated in vacuo and the residue is dissolved in methylene chloride. The organic layer is dried, filtered through a pad of hydrous magnesium silicate and the filtrate is evaporated in vacuo to give 2-and 3- chloromethyl-6-(2-(5-(3-chloro-phenyl)-2-oxo-3-oxazolidinyl)propyl)-1,4-benzodioxane. The individual, 2- and 3- isomers, are separated by chromatography.

Workup

  1. waitthe stirring is continued at room temperature for 24 hours
  2. customThe solvent is evaporated in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride
  4. customThe organic layer is dried
  5. filtrationfiltered through a pad of hydrous magnesium silicate
  6. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-7309dcca65f14953bd4de59d858c6530
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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