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CAS No. : | 1443151-85-6 | MDL No. : | MFCD16994405 |
Formula : | C12H16BClO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 254.52 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7 g | With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In N,N-dimethyl-formamide; for 2h;Reflux; | To a solution of 5 g of <strong>[183802-98-4]5-bromo-2-chlorophenol</strong> in 100 ml of DMF are added 7.5 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-l,3,2-dioxaborolane, 7.1 g of potassium acetate and then 1.97 g of tetrakis(triphenylphosphine)palladium, and the mixture is refluxed for 2 hours. The reaction mixture is concentrated under vacuum, the residue is extracted with EtOAc, the organic phase is washed with water, with 10% NaHCC solution and with saturated NaCl solution, and dried over MgS04, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a cyclohexane/EtOAc mixture in a gradient of from (100/0 v/v) to (80/20 v/v). 7 g of the expected compound are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tetrabutylammonium 2‐chlorophenyl sulfate; bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin In 1,4-dioxane at 40℃; for 14h; Glovebox; Stage #2: With hydrogenchloride In 1,4-dioxane; water for 1h; Glovebox; regioselective reaction; | ||
Stage #1: tetrabutylammonium 2‐chlorophenyl sulfate; bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol at 20℃; for 1h; Overall yield = 94 percentSpectr.; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tetraethylammonium 2‐chlorophenyl sulfate; bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin In 1,4-dioxane at 40℃; for 14h; Glovebox; Stage #2: With hydrogenchloride In 1,4-dioxane; water for 1h; Glovebox; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: pyridine; sulfur trioxide pyridine complex / dichloromethane / 19 h / 20 - 40 °C 1.2: 1 h 2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin / 1,4-dioxane / 14 h / 40 °C / Glovebox 2.2: 1 h / pH 1 - 2 / Glovebox | ||
Multi-step reaction with 2 steps 1.1: pyridine; sulfur trioxide pyridine complex / dichloromethane / 19 h / 20 - 40 °C 1.2: 1 h 2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin / 1,4-dioxane / 14 h / 40 °C / Glovebox 2.2: 1 h / pH 1 - 2 / Glovebox | ||
Multi-step reaction with 2 steps 1.1: triethylamine; chlorosulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2.2: 1 h / 20 °C |