Cesium fluoride → 4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene

HRID 2390155Notes

Reaction equation

HRID 2390155 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH:15](/B(O)O)=[CH:16]\[CH3:17].[F-].[Cs+]>CCOC(C)=O.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>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2](/[CH:15]=[CH:16]/[CH3:17])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 20603662-Bromo-5-methylsulfonylnitrobenzeneHCID 6157276((1E)-prop-1-en-1-yl)boronic acid

Product 1

HCID 585219844-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-5-methylsulfonylnitrobenzene (1.50 g; 5.36 mmol), trans-propenylboronic acid (690 mg; 8.03 mmol), caesium fluoride (2.44 g; 16.1 mmol) and bis(triphenylphosphine)palladium(II) chloride (376 mg; 0.54 mmol) was degassed with nitrogen, then treated with dioxane (30 ml) and water (15 ml). The resulting reaction mixture was heated at 80° C. for 2 hours, taken up in EtOAc and washed with water and brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as an off-white solid (1.10 g, 85%).

Workup

  1. customwas degassed with nitrogen
  2. additiontreated with dioxane (30 ml) and water (15 ml)
  3. customThe resulting reaction mixture
  4. washwashed with water and brine
  5. customThe organic phase was dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue which
  9. customwas purified by by flash column chromatography
  10. washeluting with cyclohexane containing
  11. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-96ffc12890014acbb23076d3c1607857
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…