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CAS No. : | 1007-15-4 | MDL No. : | MFCD00042466 |
Formula : | C8H6BrFO | Boiling Point : | - |
Linear Structure Formula : | C6H3BrFC(O)CH3 | InChI Key : | SZDWTGAORQQQGY-UHFFFAOYSA-N |
M.W : | 217.04 | Pubchem ID : | 70508 |
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 acetate; In 1,4-dioxane; dimethyl sulfoxide; | 1-[4-Fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]ethanone To a solution of 3-bromo-4-fluoroacetophenone (10 g, 46.07 mmol) and bis(pinacolato)diboron (12.87 g, 50.68 mmol) in 1,4-dioxane (90 ml) and DMSO (10 ml) was added potassium acetate (9.04 g, 92.14 mmol) and the mixture degassed for 1 h. Dichloro[1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane (DCM) adduct (1.13 g, 1.38 mmol) was added and the mixture degassed for a further 15 min and then heated at 90 C. for 18 h. After cooling to ambient temperature the mixture was filtered and the filter cake washed with ethyl acetate (2*50 ml). The filtrate was then washed with water (100 ml), brine (100 ml), dried (MgSO4), filtered and evaporated to give the title product as a brown oil which was used without further purification (12.0 g): δH (400 MHz, CDCl3) 1.38 (12H, s), 2.61 (2H, s), 2.61 (3H, s), 7.10 (1H, t, J 8.6 Hz), 8.05-8.09 (1H, m), 8.35 (1H, dd, J 2.3, 5.5 Hz). | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110.0℃; for 0.166667h;Microwave irradiation; | General procedure: To 2 mL of 1,4-dioxane in microwave reaction vessel were added bromobenzene (0.20 g, 1.27 mmol), bis(pinacolato)diboron (0.36 g, 1.40 mmol), potassium acetate (0.38 g, 3.8 mmol), and PdCl2(dppf) (0.028 g, 0.038 mmol). The reaction mixture was heated to 110 C by microwave irradiation at power 100 W for 10 min. After solvent was removed under reduced pressure, the residue was purified by dry column vacuum chromatography (DCVC) using dichloromethane (DCM) as eluent provided the 0.16 g in 62 % yield; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1-Bromo-3-[1-(4-methoxy-3-chlorophenyl)-vinyl]-6-fluorobenzene A solution of n-butyllithium (1.6 M solution in hexane, 20 mL, 1.1 eq) was added dropwise to a solution of <strong>[50638-47-6]4-bromo-2-chloro-1-methoxy-benzene</strong> (6 g, 27 mmol, 1 eq) in tetrahydrofuran (25 mL) at -78 C. After stirring 30 min 3-bromo-4-fluoroacetophenone (5.8 g, 27 mmol, 1 eq) in tetrahydrofuran (25 mL) was added dropwise. The mixture was allowed to warm up to room temperature and stirred for 2 h, then treated with water (10 mL), extracted with ethyl acetate, dried (sodium sulfate) and concentrated in vacuo. The crude was dissolved in acetic acid (80 mL) and concentrated sulfuric acid (17 mL) was added. The mixture was warmed to 75 C. for 30 min, cooled at room temperature and neutralized with 1 N NaOH. The aqueous phase was extracted with dichloromethane (3*100 mL), dried (sodium sulfate) the solvent was removed under reduced pressure. The residue was purified by column chromatography (cyclohexane) to afford the title compound as a colourless oil (3.2 g, 36%); Mass (calculated) C15H11BrClFO [341]; (found) [M+H+]=342 LC Rt=3.05 min (5 min method) 1H-NMR (CDCl3): 3.90 (s, 3H), 5.35 (d, 2H), 6.88 (m, 1H), 7.06-7.26 (m, 4H), 7.50 (m, 1H) |
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