Water → HCID 59259711, compound

HRID 642968Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O1[CH2:19][CH2:18][O:17][CH2:16]C1.O.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:27][CH2:28]CCCCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:19]1([CH2:18][O:17][CH2:16][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 4-chlorobiphenyl (50 mg, 265 μmol) and 1,4-dioxane (2 ml) were added water (0.2 ml), cesium carbonate (259 mg, 795 μmol), potassium cyclopropylmethoxymethyl trifluoroborate (102 mg, 530 mol), palladium (II) acetate (5.95 mg, 27 μmol) and 2-dicycrohexylphospino-2′,6′-dimethoxybiphenyl (21.8 mg, 53.1 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 7 hours and 30 minutes. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the title compound (57 mg, 239 μmol, 90%).

Workup

custom30 minutes
temperatureAfter the reaction mixture was cooled at room temperature
filtrationfollowed by filtration
washThe separated organic layer was washed with an aqueous saturated sodium chloride solution
customThe organic layer was separated
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1)

Sources & evidence

ORD record: ord-ff18346e62c74d9a87fb81ed027478bb
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696347B2

Reaction notes

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