Iodobenzene → 4-(3-Phenyl-1,1-dimethyl-2-propynyl)anisole

HRID 481534Notes

Reaction equation

HRID 481534 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)([CH3:5])[C:3]#[CH:4].[C:14]1(I)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:14]1([C:4]#[C:3][C:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)([CH3:1])[CH3:5])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 11575IodobenzeneHCID 183336214-(1,1-Dimethyl-2-propynyl)anisole

Product 1

HCID 122773974-(3-Phenyl-1,1-dimethyl-2-propynyl)anisoleYield 84%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

To a stirred solution of Compound 21 (299 mg, 1.72 mmol), PhI (385 mg, 1.89 mmol), and (PPh3)2PdCl2 (60 mg, 0.086 mmol) in Et2NH (10 ml) was added CuI (33 mg, 0.17 mmol) at r.t. under N2, and stirred for 18 h. The mixture was quenched by the addition of H2O, and extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 67 (360 mg, 84%) as a colorless oil.

Workup

  1. customThe mixture was quenched by the addition of H2O
  2. extractionextracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-ea11fe7153784776b12df042cf89408d
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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