1,3-Dibromopropane → 3-Phenyl-6-(3-bromopropyloxy)-7-propylbenzofuran

HRID 342764Notes

Reaction equation

HRID 342764 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([OH:19])=[C:15]([CH2:16][CH2:17][CH3:18])[C:10]=3[O:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Br:26][CH2:27][CH2:28][CH2:29]Br>C(C(C)=O)C>[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:19][CH2:29][CH2:28][CH2:27][Br:26])=[C:15]([CH2:16][CH2:17][CH3:18])[C:10]=3[O:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 154629143-Phenyl-7-propyl-1-benzofuran-6-ol

Product 1

HCID 540110163-Phenyl-6-(3-bromopropyloxy)-7-propylbenzofuran

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3-phenyl-6-hydroxy-7-propylbenzofuran (3.54 g, 13.99 mmol) and potassium carbonate (2.08 g, 15.05 mmol) in dry methyl ethyl ketone (50 ml) was added 1,3-dibromopropane (2.84 ml, 27.98 mmol). The reaction mixture refluxed for 5 hours under nitrogen. The mixture was partitioned between isopropyl acetate and pH4 buffer. The organic was dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by chromatography (silica gel, 50% methylene chloride in hexane) to afford the title compound.

Workup

  1. temperatureThe reaction mixture refluxed for 5 hours under nitrogen
  2. customThe mixture was partitioned between isopropyl acetate and pH4 buffer
  3. dry with materialThe organic was dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography (silica gel, 50% methylene chloride in hexane)

Sources & evidence

ORD record
ord-ce050a1f179443c59535ece0b2a55081
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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