1,3-Dibromopropane → HCID 15157498, compound

HRID 2371615Notes

Reaction equation

HRID 2371615 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][CH2:14][CH2:13][Br:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 960094-Hydroxyphenylacetate

Product 1

HCID 15157498HCID 15157498, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.52 g (10 mmol) of 4-acetoxyphenol, 2.22 g (11 mmol) 1,3-dibromopropane, and 2.98 g (21 mmol) of anhydrous potassium carbonate in dimethylformamide was stirred rapidly at room temperature for 4 hours. Ethyl acetate was added, and the salts present were removed by filtration. The solvent was removed under reduced pressure, and the residue chromatographed over silica gel. Elution with 15% ethyl acetate-hexane gave 270 mg of the title compound, which was homogeneous by thin layer chromatography (15% by volume of ethyl acetate/hexane on silica gel plates).

Workup

  1. customthe salts present were removed by filtration
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed over silica gel
  4. washElution with 15% ethyl acetate-hexane

Sources & evidence

ORD record
ord-9136c2a18f72446e9d21c7913bd99bd2
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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