1,10-Phenanthroline → Benzene, 1-methoxy-4-(1-methylethoxy)-

HRID 1243053Notes

Reaction equation

HRID 1243053 reaction equation
N1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2N=CC=C3)C=CC=1.[C:15]([O-:18])([O-])=O.[Cs+].[Cs+].IC1C=[CH:26][C:25]([O:28]C)=[CH:24]C=1>[Cu]I.C(O)(C)C>[CH:25]([O:28][C:5]1[CH:6]=[CH:7][C:8]([O:18][CH3:15])=[CH:13][CH:14]=1)([CH3:26])[CH3:24]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 696764-Iodoanisole

Product 1

HCID 140757Benzene, 1-methoxy-4-(1-methylethoxy)-Yield 415.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol %), 1,10-phenanthroline (36 mg, 0.20 mmol, 20 mol %), Cs2CO3 (456 mg, 1.4 mmol), 4-iodoanisole (234 mg, 1.0 mmol) and isopropanol (1.0 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 23 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane/ethyl acetate 20:1) provided 138 mg (83% yield) of the title compound as a colorless oil.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customPurification of the residue by flash chromatography on silica gel (2×20 cm; hexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-a1c8ed6d713741ea8cffc7d474e923d1
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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