Methanol → 3-Methoxybenzonitrile

HRID 1883409Notes

Reaction equation

HRID 1883409 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:15]([O-])([O-])=[O:16].[Cs+].[Cs+].I[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26].CO>[Cu]I.C1(C)C=CC=CC=1>[CH3:15][O:16][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26]

Participants

7

Reactant 4

HCID 887MethanolHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1443413-Iodobenzonitrile

Product 1

HCID 737123-MethoxybenzonitrileYield 84%

Reagents, catalysts & solvents 2

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

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 (652 mg, 2.0 mmol), 3-iodobenzonitrile (229 mg, 1.0 mmol), methanol (162 μL, 4.0 mmol) and toluene (1 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 diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 5:1) provided 111 mg (84% 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 5:1)

Sources & evidence

ORD record
ord-2f6a049d14934dd79e56c8f960604918
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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