1,3-Dibromopropane → HCID 13505602, compound

HRID 465144Notes

Reaction equation

HRID 465144 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:17](=[O:19])[CH3:18])[C:10]([OH:16])=[CH:11][CH:12]=2)[CH:7]=1.[Br:21][CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:17](=[O:19])[CH3:18])[C:10]([O:16][CH2:24][CH2:23][CH2:22][Br:21])=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 13504771HCID 13504771, compound

Product 1

HCID 13505602HCID 13505602, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.989 g of [(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]acetic acid methyl ester, 18 ml of 1,3-dibromopropane and 3.7 g of anhydrous potassium carbonate in 150 ml of anhydrous acetone was stirred at reflux for 16.5 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed on 250 g of silica gel. Elution with 10% ethyl acetate-toluene gave 6.730 g (95% yield) of [[8-acetyl-7-(3-bromopropoxy)-2-naphthalenyl]oxy]acetic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 16.5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on 250 g of silica gel
  5. washElution with 10% ethyl acetate-toluene

Sources & evidence

ORD record
ord-798922f634ca4c789108c75fe832aa69
Source dataset
uspto-grants-1985_10
Patent number
US04550190

Reaction notes

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