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

HRID 2179227Notes

Reaction equation

HRID 2179227 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.I[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[CH:24]([OH:27])([CH3:26])[CH3:25]>[Cu]I>[CH:24]([O:27][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 13181,10-PhenanthrolineHCID 3776IsopropanolHCID 696764-Iodoanisole

Product 1

HCID 140757Benzene, 1-methoxy-4-(1-methylethoxy)-Yield 83%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

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-d612a1f99e604054b0f26782572b6737
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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