Cesium carbonate → 4-Methoxy-2-nitro-biphenyl

HRID 1518633Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(OB(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Bromo-4-methoxy-2-nitrobenzene (2.32 g, 10 mmol) was dissolved in 1,4-dioxane (30 mL) and, thereto, were added phenyl boric acid (2.44 g, 20 mmol), cesium carbonate (26 g, 80 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.82 g, 1 mmol), and purified water (12 mL). The reaction mixture was stirred under a nitrogen flow at 80° C. for 18 hours. The reaction solution was filtered through celite, alumina, and Florisil, and, thereafter, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 4-methoxy-2-nitro-1-phenylbenzene (1.86 g).

Workup

custompurified water (12 mL)
filtrationThe reaction solution was filtered through celite, alumina, and Florisil
extractionextracted with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-44fedd1f22a34adb8e981105e0614b93
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09072734B2

Reaction notes

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