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CAS No. : | 5122-94-1 | MDL No. : | MFCD00093311 |
Formula : | C12H11BO2 | Boiling Point : | - |
Linear Structure Formula : | (C6H5)(C6H4)B(OH)2 | InChI Key : | XPEIJWZLPWNNOK-UHFFFAOYSA-N |
M.W : | 198.03 | Pubchem ID : | 151253 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With potassium carbonate;FibreCat; In ethanol; water; at 110℃; for 0.13333299999999998h;Microwave irradiation; | A 5 mL Biotage microwave vial was charged with FibreCat (Aldrich, 0.4 mmol/g; 37.5 mg, 3 mol%) and biphenyl-4- boronic acid (1 19.0 mg, 0.600 mmol). A solution of S-chloro^-iodo^-nitro-phenylamine (Intermediate 1, 149.0 mg, 0.500 mmol) in EtOH (4.4 mL) was added followed by IM aqueous K2CO3 (0.6 mL). The vial was heated in a microwave synthesizer (Biotage Initiator) at 1100C for 8 min. Contents of the vial were diluted with EtOAc (2 mL) and filtered. The resulting precipitate was washed with EtOAc (three times, 2 mL). The filtrate and washes were combined and evaporated to dryness in vacuo. The residue was dissolved in EtOAc (4 mL), washed with 1 M aqueous K2CO3 (twice, 1 mL) and evaporated to dryness in vacuo to give an orange-yellow solid. LR-MS (API-ES): calculated for Ci8Hi3ClN2O2 324.1, observed m/e 367.2 (100%), 347.0 ((M + Na)+, 325.0 (M + H)+, (Rt 3.56 min). The crude product was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
109 mg | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide; In tert-Amyl alcohol; at 50℃; for 20h;Inert atmosphere; | General procedure: Amixture of phenylboronic acid (1a) (1 mmol, 122 mg), alpha-trifluoromethylacrylicacid (2) (0.5 mmol, 70 mg), [Cp*RhCl2]2 (0.01 mmol, 6 mg), AgSbF6 (0.1 mmol, 34mg), Ag2O (1 mmol, 232 mg), and 1-methylnaphthalene (ca. 40 mg) as internal standard was stirred in tert-amylalcohol (3 ml) under argon at 50 C for 20 h.Then the reaction mixture was diluted by ethyl acetate (30 ml). The organiclayer was washed by 1 N HCl(30 ml), water 30 (ml), and brine (30 ml) and driedover Na2SO4. After evaporation of the solvents under vacuum, product 3a? (101 mg,93%) was isolated by column chromatography on silica gel usinghexane/EtOAc/AcOH=90/9/1 (v/v/v) as eluent. |