Triethylamine → 2-Methoxy-4-nitro-1-(phenylethynyl)benzene

HRID 705338Notes

Reaction equation

HRID 705338 reaction equation
C(N(CC)CC)C.I[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[O:18][CH3:19].[C:20]1([C:26]#[CH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[CH3:19][O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[C:27]#[C:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 2301031-Iodo-2-methoxy-4-nitrobenzene

Product 1

HCID 116085312-Methoxy-4-nitro-1-(phenylethynyl)benzeneYield 98%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of triethylamine (60 mL) and tetrahydrofuran (20 mL) were added 1-iodo-2-methoxy-4-nitrobenzene (10 g, 35.8 mmol) and bis(triphenylphosphine)palladium (II) chloride (0.503 g, 0.717 mmol). Phenylacetylene (4.48 g, 43.0 mmol) in tetrahydrofuran (10 mL) was added dropwise to the reaction mixture and the mixture was stirred for 5 minutes. Copper iodide (0.068 g, 0.358 mmol) was added, and the reaction mixture was stirred and purged with nitrogen for 10 minutes. The reaction flask was sealed and stirred for 2 hours at room temperature. The reaction mixture was treated with 200 mL of dichloromethane, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo leaving a solid. The crude solid was recrystallized from absolute ethanol. The solid was collected by filtration and washed with cold ethanol and dried in vacuo to give the title compound as a tan solid (8.87 g, 98%).

Workup

  1. stirringthe reaction mixture was stirred
  2. custompurged with nitrogen for 10 minutes
  3. customThe reaction flask was sealed
  4. stirringstirred for 2 hours at room temperature
  5. additionThe reaction mixture was treated with 200 mL of dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customleaving a solid
  11. customThe crude solid was recrystallized from absolute ethanol
  12. filtrationThe solid was collected by filtration
  13. washwashed with cold ethanol
  14. customdried in vacuo

Sources & evidence

ORD record
ord-c6cc85cac0bc4bb9850bf43697e21e4a
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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