2-Bromo-5-nitroanisole → HCID 66858326, compound

HRID 1803131Notes

Reaction equation

HRID 1803131 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([Sn](CCCC)(CCCC)CCCC)[O:4][N:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[O:30][CH3:31]>O1CCOCC1.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>[CH3:31][O:30][C:22]1[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=1[C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1

Participants

5

Reactant 2

HCID 1012932-Bromo-5-nitroanisoleHCID 27632553-Methyl-5-(tributylstannyl)isoxazole

Product 1

HCID 66858326HCID 66858326, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

Step H (1): 3-Methyl-5-(tributylstannyl)isoxazole (2.4 g, 6.4 mmol, H. Yamanaka et. al Tetrahedron, 1991, 47, 5111) and dichlorobis(triphenylphosphine)palladium (II) (45 mg, 0.0643 mmol) were added to a degassed solution of 1-bromo-2-methoxy-4-nitrobenzene (1.26 g, 5.5 mmol) in dioxane (25 mL). The resulting mixture was heated to reflux (105° C. oil bath temperature) for 24 h. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatography to afford 5-(2-methoxy-4-nitrophenyl)-3-methylisoxazole (600 mg, 40% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureThe reaction mixture was cooled to rt
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified

Sources & evidence

ORD record
ord-137f9976f8264eed9f3e1e94860649a2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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