Water → 1-(Phenylethynyl)-4-(phenylsulfonyl)benzene

HRID 2376978

Reaction equation

HRID 2376978 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.[Cu]I.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>[C:19]1([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:11])=[CH:7][CH:8]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11575IodobenzeneHCID 199393204-Phenylsulfonylphenylethyne

Product 1

HCID 210994031-(Phenylethynyl)-4-(phenylsulfonyl)benzeneYield 28%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-ethynyl-4-(phenylsulfonyl)benzene (100 mg, 0.4 mmol), iodobenzene (0.05 mL, 0.44 mmol) and triethylamine (1 mL) in toluene (1 mL) was degassed. Copper(I) iodide (3 mg, 0.004 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (3 mg, 0.004 mmol) were added and the reaction stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (35 mg, 28%). δH (500 MHz, d6 DMSO): 7.97 (4H, dd, J=2.6, 8.4 Hz), 7.77-7.69 (3H, m), 7.64-7.56 (4H, m), 7.43-7.41 (3H, m).

Workup

  1. customwas degassed
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ba9a3283617640d78ac445ed19ea65b5
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Linked notes

Loading…