1-Butanol → 3-Butoxybenzonitrile

HRID 1243057

Reaction equation

HRID 1243057 reaction equation
CC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C([O-])([O-])=O.[Cs+].[Cs+].I[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27].[CH2:31]([OH:35])[CH2:32][CH2:33][CH3:34]>[Cu]I.C1(C)C=CC=CC=1>[CH2:31]([O:35][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27])[CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 10796Cesium carbonateHCID 727915-Methyl-1,10-phenanthrolineHCID 1443413-Iodobenzonitrile

Product 1

HCID 219407163-ButoxybenzonitrileYield 87%

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 %), 5-methyl-1,10-phenanthroline (39 mg, 0.20 mmol, 20 mol %), Cs2CO3 (652 mg, 2.0 mmol), 3-iodobenzonitrile (229 mg, 1.0 mmol), n-butanol (366 μL, 4.0 mmol) and toluene (1 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 28 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 30:1) provided 152 mg (87% 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 30:1)

Sources & evidence

ORD record
ord-a0a46c0606df4b4ca81386fc0d98f686
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Linked notes

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