1,3-Dibromopropane → 3245-62-3

HRID 2371612Notes

Reaction equation

HRID 2371612 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:15][CH2:14][CH2:13][Br:12]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 86632-NaphtholHCID 11430Potassium Carbonate

Product 1

HCID 41136723245-62-3Yield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.60 g (25 mmol) of 2-naphthol and 6.0 g (30 mmol) of 1,3-dibromopropane in dimethylformamide was added 7.25 g (52.5 mmol) of finely ground anhydrous potassium carbonate. The mixture was stirred vigorously overnight. Solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was further extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, and after filtration, the solvent was removed under reduced pressure. The residue was then chromatographed over silica gel using 10% methylene chloride/hexane as eluent to afford 1.66 g of the title compound, which was homogeneous by thin layer chromatography (5% by volume of ethyl acetate/hexane on silica gel plates).

Workup

  1. customSolvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was further extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationafter filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was then chromatographed over silica gel using 10% methylene chloride/hexane as eluent

Sources & evidence

ORD record
ord-6704f6db47374a298a6ca35aace22265
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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