Cesium carbonate → p-methoxymethylnitrobenzene

HRID 642965Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=O)=O.[O:18]1[CH2:23]COC[CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.O>[CH3:19][O:18][CH2:23][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of 4-nitrophenyl trifluoromethanesulfonate (30 mg, 0.11 mmol) and 1,4-dioxane (3 ml) were added water (0.3 ml), cesium carbonate (0.11 g, 0.34 mmol), potassium methoxymethyl trifluoroborate (17 mg, 0.11 mmol),palladium (II) acetate (1.3 mg, 0.0056 mmol) and tri-o-tolylphosphine (8.5 mg, 0.028 mmol). Then, the reaction mixture was stirred at 95° C. (external temperature) for 4 hours. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, and the organic layer was separated. The organic layer was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (13 mg, 0.078 mmol, 68%).

Workup

temperatureAfter the reaction mixture was cooled at room temperature
customthe organic layer was separated
filtrationThe organic layer was filtered
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-6fab8db13c6e43bcb669e4b6e7648165
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696347B2

Reaction notes

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