Diisopropylamine → 1-Bromo-3-(2-phenylethynyl)benzene

HRID 530414Notes

Reaction equation

HRID 530414 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(NC(C)C)(C)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:16]#[C:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 10821PhenylacetyleneHCID 11561Benzene, 1-bromo-3-iodo-

Product 1

HCID 158361061-Bromo-3-(2-phenylethynyl)benzene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1-bromo-3-iodobenzene (15.3 g, 54.0 mmol), phenylacetylene (5 g, 49.0 mmol), tetrakis(triphenylphosphine)palladium (2.8 g, 2.4 mmol) and copper(I) iodide (0.46 g, 2.4 mmol) were dissolved in dry toluene and diisopropylamine (35 mL, 196 mmol) under a nitrogen atmosphere. The reaction was stirred at room temperature overnight. The mixture was extracted with ethyl acetate and the organic layer was dried in vacuo to give the title compound as a residue that was used without further purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe organic layer was dried in vacuo

Sources & evidence

ORD record
ord-a2df377c2a7045e9b9d4e0583c436a6a
Source dataset
uspto-grants-2016_05
Patent number
US09353089B2

Reaction notes

Loading…