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CAS No. : | 2675-79-8 | MDL No. : | MFCD00017169 |
Formula : | C9H11BrO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | XAOOZMATJDXDQJ-UHFFFAOYSA-N |
M.W : | 247.09 | Pubchem ID : | 75885 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280 | UN#: | |
Hazard Statements: | H317 | 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 |
---|---|---|
71% | 5-Bromo-1,2,3-trimethoxybenzene (1.60 g, 6.47 mmol) was dissolved in THF (50 mL) and cooled to -78 C. n-BuLi (2.7 mL, 6.8 mmol) was added dropwise, and the reaction mixture was stirred for 1 h. Ketone 11 (0.92 g, 4.79 mmol) was dissolved in THF (10 mL) and added dropwise to the reaction flask, and the mixture was stirred for 12 h while warming to room temperature, at which time it was washed with water, extracted with EtOAc (3*30 mL), dried over sodium sulfate, concentrated, and purified by flash chromatography using a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexane; gradient: 10% A/90% B (1 CV), 10% A/90% B?80% A/20% B (10 CV), 80% A/20% B (1 CV); flow rate: 50 mL/min; monitored at 254 nm and 280 nm] to afford tertiary alcohol 25 (1.221 g, 3.39 mmol, 71%) as an orange oil. NMR data was collected after the subsequent step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.9% | With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 100 - 108℃; for 8h;Inert atmosphere; | The reaction route is as follows:250mL three-necked flask was added 2.71g (0.01mol)1,1-bis (4-aminophenyl) cyclohexane,11.31 g (0.046 mol) of 3,4,5-trimethoxybenzene,5.71 g (0.051 mol) potassium t-butoxide,54.2 g toluene.Under nitrogen atmosphere, 0.373 g (4.1 10-4 mol) of Pd2 (dba) 3,0.236 g (8.1 × 10 -4 mol) (t-Bu) 3PH · BF 4,The temperature was raised to 100 C to 108 C and refluxed for 8 hours.Completed the reaction,Add 50g water twice,Dried over anhydrous sodium sulfate,Decompression solvent was brown viscous liquid.The above crude product was treated with THF,Ethyl acetate (mass ratio of 5: 5) recrystallization,6.8g white powder was obtained,Yield: 71.9%. |
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