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

HRID 449115Notes

Reaction equation

HRID 449115 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:29])[CH2:28][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:29][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 7966CyclohexanolHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 111397141-Bromo-4-(cyclohexyloxy)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 cyclohexanol (1.770 g, 17.67 mmol) in toluene (1.500 mL) was added copper(I) iodide (135 mg, 0.707 mmol) and Cs2CO3 (2.879 g, 8.837 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). 1H NMR (400 MHz, MeOD) δ1.32-1.65 (m, 6H), 1.77-1.86 (m, 2H), 1.94-2.03 (m, 2H), 4.24-4.37 (m, 1H), 6.81-6.90 (m, 2H), 7.36-7.41 (m, 2H).

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-b77e5d8b08ae4219a558cc43103817ab
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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