Stannane, tributyl(1-ethoxyethenyl)- → HCID 67167386, compound

HRID 2093781Notes

Reaction equation

HRID 2093781 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC>CN(C=O)C>[CH3:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([CH3:8])=[CH:7][C:2]=1[C:18](=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 8258081-Bromo-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 67167386HCID 67167386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1-Bromo-2,5-dimethyl-4-nitrobenzene (1 g, 4.34 mmol) and tributyl(1-ethoxyvinyl)tin (1.88 g, 5.2 mmol) in DMF (20 mL), was added tetrakis(triphenylphospine) palladium (0) (250 mg, 5% mmol). The reaction tube was sealed, the mixture was purged with N2 for 3 min and then heated at 90° C. under N2 for overnight. The reaction was cooled to room temperature and poured into aqueous HCl (1N, 100 mL). The mixture was stirred for 1 hour, and then extracted with ethyl acetate (3×100 mL). The organic extracts were combined, washed with brine and concentrated. The crude product was purified with silica gel chromatography (20% ethyl acetate in hexanes) to afford 1-(2,5-dimethyl-4-nitrophenyl)ethanone as a yellow solid.

Workup

  1. customThe reaction tube was sealed
  2. customthe mixture was purged with N2 for 3 min
  3. temperatureThe reaction was cooled to room temperature
  4. additionpoured into aqueous HCl (1N, 100 mL)
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. washwashed with brine
  7. concentrationconcentrated
  8. customThe crude product was purified with silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8cb7f77b40754ae2b02994dcd1ff1e33
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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