3-Methylbut-1-yne → 4-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

HRID 40130

Reaction equation

HRID 40130 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][CH:14]([CH3:17])[C:15]#[CH:16]>CCN(CC)CC.CN(C=O)C.[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>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][CH:14]([CH3:17])[CH3:13])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

7

Reactant 2

HCID 690193-Methylbut-1-yneHCID 2926594-Iodo-3-nitroanisole

Product 1

HCID 597623514-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (Aldrich, 10 g, 35.8 mmol) in Et3N (60 ml) and DMF (6 ml) was added CuI (34 mg, 0.18 mmol), Pd(PPh3)2Cl2 (126 mg, 0.18 mmol), and 3-methyl-1-butyne (5.0 ml, 73.5 mmol). The mixture was stirred at room temperature for 16 h and was concentrated. The resulting mixture was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes) to yield the title compound as a brown oil.

Workup

  1. concentrationwas concentrated
  2. additionThe resulting mixture was diluted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b7a226b1c835495eaf8a21b6a00f0eb4
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Linked notes

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