Cesium carbonate → HCID 59398554, compound

HRID 2070038Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([OH:19])[CH2:16][C:17]#[CH:18].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>O1CCOCC1.[Cu](I)I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]#[C:17][CH2:16][CH2:15][OH:19])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Bromo-3-(trifluoromethyl)nitrobenzene (500 mg, 1.85 mmol) was dissolved in 1,4-dioxane (10 mL), and but-3-yn-1-ol (389 mg, 5.56 mmol), copper iodide (35 mg, 0.18 mmol), palladium acetate (21 mg, 5 mol %), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl bisphenyl (88 mg, 10 mol %), and cesium carbonate (1207 mg, 3.70 mmol) were added thereto. The resulting mixture was stirred under nitrogen atmosphere at 80° C. for 10 hours, and a saturated ammonium chloride aqueous solution was added thereto to quench the reaction. The reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4-(4-nitro-2-(trifluoromethyl)phenyl)but-3-yn-1-ol (160 mg, 33%) as a brown oil.

Workup

customto quench
customthe reaction
extractionThe reaction solution was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
concentrationconcentrated under reduced pressure
customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-04d99576c5124cb89ce02fa12caffc32
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299252B2

Reaction notes

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