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CAS No. : | 78495-63-3 | MDL No. : | MFCD02179483 |
Formula : | C7H8BFO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | XOVMDVZAWWQSDC-UHFFFAOYSA-N |
M.W : | 169.95 | Pubchem ID : | 3294524 |
Synonyms : |
|
Chemical Name : | 2-Fluoro-6-methoxyphenylboronic acid |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | 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 |
---|---|---|
63% | With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In tetrahydrofuran; water; toluene; at 60℃; for 18h; | a) 1-Bromo-2,3-difluorobenzene (3.00 g, 15.45 mmol)and 2-fluoro-6-methoxybenzeneboronic acid (3.96 g, 23.32 mmol) were dissolved in THF (78 mL). To thissolution potassium fluoride (2.71 g, 46.64 mmol) dissolved in water (8 mL) was added. Tothis solution tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3) (711 mg, 0.78 mmol) and 1 M tri-tert-butylphosphine (tBu3P) in toluene (1.55 mL) were added, and then the mixturewas stirred at 60 °C for 18 h. After the reaction mixture was cooled to room temperature, a solid was removed by filtration. To the filtrate was water added, and the aqueous layer wasextracted with tert-butyl methyl ether. The combined organic layer was washed with brine.After drying over MgSO4, the solvent was removed under reduced pressure to give yellowish oil. The crude product was purified by column chromatography on silica gel eluting with a mixed solvent of heptane and tert-butyl methyl ether (95:5) to yield 2.33 g (63percent) of 1,2- difluoro-3-(2-fluoro-6-methoxy-phenyl)benzene (C-i) as a yellow oil.1HNMR (300 MHz, CDCI3): 6 7.40-7.33 (m, 2H), 7.25-7.10 (m, 3H), 6.85-6.80 (m, 2H),3.82 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.41 g | With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium carbonate; In 1,2-dimethoxyethane; water; at 110℃; for 1.5h;Microwave irradiation; | A mixture of <strong>[126717-59-7]3-bromo-6-methoxy-2-picoline</strong> (CAS No. 126717-59-7) (1 g, 4.95 mmol, 1 equivalent), (2-fluoro-6-methoxyphenyl)boronic acid (CAS No. 78495-63-3) (925 mg, 5.44 mmol, 1.1 equivalents), (Ataphos)2PdCl2 (175 mg, 0.247 mmol, 0.05 equivalents), sodium carbonate (787 mg, 7.42 mmol, 1.5 equivalents), DME (15 mL) and water (5 mL) was reacted in a microwave reactor at 110 C. for 1.5 hours. A total of four similar reactions were performed, and then worked up together. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (NH silica gel on silica gel, 0%-20% ethyl acetate/n-heptane) to afford the title compound (3.41 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.26 (s, 3H), 3.77 (s, 3H), 3.96 (s, 3H), 6.59-6.69 (m, 1H), 6.74-6.83 (m, 2H), 7.30 (td, J=8.4, 6.6 Hz, 1H), 7.37 (d, J=8.6 Hz, 1H). |
A480507[ 1599432-41-3 ]
2-(2-Fluoro-6-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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