1,10-Phenanthroline → 1-Ethoxy-3-methoxybenzene

HRID 1883406Notes

Reaction equation

HRID 1883406 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+].IC1[CH:23]=[C:24]([O:28]C)C=CC=1>[Cu]I.C(O)C>[CH2:24]([O:28][C:14]1[CH:13]=[C:8]([O:18][CH3:15])[CH:7]=[CH:6][CH:5]=1)[CH3:23]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 69839Benzene, 1-iodo-3-methoxy-

Product 1

HCID 1412411-Ethoxy-3-methoxybenzeneYield 466.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolvent

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), 3-iodoanisole (119 μL, 1.0 mmol) and ethanol (1.0 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 20 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 30:1) provided 142 mg (93% 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 diethyl ether
  4. concentrationThe filtrate was concentrated
  5. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 30:1)

Sources & evidence

ORD record
ord-822fff2a76d7401488bbc79e2ecb7cbb
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

Loading…