1,10-Phenanthroline → 1-Bromo-4-(cyclopentyloxy)benzene

HRID 449114Notes

Reaction equation

HRID 449114 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C1C=NC2C3N=CC=CC=3C=CC=2C=1.[CH:23]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:28][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 7298CyclopentanolHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 225999581-Bromo-4-(cyclopentyloxy)benzene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 1-bromo-4-iodo-benzene, (1.00 g, 3.53 mmol), o-phenanthroline (255 mg, 1.41 mmol) and cyclopentanol (1.50 g, 17.44 mmol) in toluene (1.500 mL) was added copper(I) iodide (135.00 mg, 0.70 mmol) and Cs2CO3 (2.87 g, 8.83 mmol). The resulting mixture was then stirred at 120° C. in a sealed tube for 15 hours. The solvent was then removed under reduced pressure and the product was purified by flash chromatography (eluted by hexane).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe product was purified by flash chromatography (eluted by hexane)

Sources & evidence

ORD record
ord-2e6af75726804d49a308d65bbd65f981
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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