1,5-Dibromopentane → HCID 54389898, compound

HRID 465145Notes

Reaction equation

HRID 465145 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][CH2:25][CH2:26]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][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][Br:21])=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 13504771HCID 13504771, compound

Product 1

HCID 54389898HCID 54389898, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.1 g of [[8-acetyl-7-hydroxy-2-naphthalenyl]oxy]acetic acid methyl ester, 9.2 g of 1,5-dibromopentane and 0.83 g of anhydrous potassium carbonate in 30 ml of anhydrous acetone was stirred at reflux for 17 hours. The reaction mixture was filtered and filtrate was concentrated at 60° C./10.15 mm to an oil which was purified by flash column chromatography to yield 1.7 g of [[8-Acetyl-7-(5-bromopentyloxy)-2-naphthalenyl]oxy]acetic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 17 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationfiltrate was concentrated at 60° C./10.15 mm to an oil which
  4. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-c9a3214af5a744df8fc1542f962e5c55
Source dataset
uspto-grants-1985_10
Patent number
US04550190

Reaction notes

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