1-Bromo-4-iodobenzene → HCID 53472883, compound

HRID 1359961Notes

Reaction equation

HRID 1359961 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][C:4]#[CH:5].[Br:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1>C(NC(C)C)(C)C.[Cu]I>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:5]#[C:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 115221-Bromo-4-iodobenzeneHCID 81643N,N-Dimethylpropargylamine

Product 1

HCID 53472883HCID 53472883, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7912DiisopropylamineSolvent

Procedure

Copper(I) iodide (17.4 mg, 0.0913 mmol), 0.113 ml (1.06 mmol) of N,N-dimethylprop-2-yn-1-amine, and 67.8 mg (0.0966 mmol) of bistriphenyl phosphine palladium dichloride were added in that order to a solution of 280.8 mg (0.993 mmol) of 1-bromo-4-iodobenzene in diisopropylamine (2 ml), and the mixture was stirred at room temperature for 50 min. The reaction solution was filtered through Celite. The solvent was removed by distillation, and the residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 0:100) to give 248.4 mg (yield 99%) of the title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customThe solvent was removed by distillation
  3. customthe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 0:100)

Sources & evidence

ORD record
ord-e035886fb22140d5b5e043435e63c757
Source dataset
uspto-grants-2011_02
Patent number
US07879808B2

Reaction notes

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