o-Iodoanisole → 4-[1,1-Dimethyl-3-(2-methoxyphenyl)-2-propynyloxy]benzonitrile

HRID 1073965Notes

Reaction equation

HRID 1073965 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[CH3:10][C:11]([CH3:23])([O:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[C:12]#[CH:13]>C(NCC)C.[Pd](Cl)Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][C:11]([CH3:23])([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=1)[C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

7

Reactant 2

HCID 68257o-IodoanisoleHCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

Product 1

HCID 198956454-[1,1-Dimethyl-3-(2-methoxyphenyl)-2-propynyloxy]benzonitrileYield 34%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

2.34 g of 2-iodoanisole were added at room temperature to a solution of 9 mg of palladium(II) chloride, 26 mg of triphenylphosphine and 19 mg of copper(I) iodide in 25 ml of diethylamine. This mixture was treated with 1.85 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile and the resulting mixture was stirred for 48 hours. The mixture was evaporated and the residue was dissolved in a mixture of ethyl acetate and water. The organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution to give 0.99 g of 4-[1,1-dimethyl-3-(2-methoxyphenyl)-2-propynyloxy]benzonitrile in the form of an oil.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-12a062c8c4ef47dcbd2fdb0bd07630d6
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

Loading…