| 77% |
With triphenylphosphine In benzene at 140℃; for 50h; |
|
| 76% |
With triphenylphosphine In toluene at 120℃; for 100h; Inert atmosphere; |
|
| 75% |
With triphenylphosphine In toluene at 140℃; for 96h; Inert atmosphere; |
3.1
(1) The benzophenone (10mmol),Carbon tetrabromide (20mmol)And triphenylphosphine (40mmol) mixture was vacuumed and filled with N2 three times,Then, 500 mL of anhydrous toluene was added and reacted at 140°C for 4 days.After cooling to room temperature,Filter the mixture,Wash with dichloromethane,And collect the filtrate,Wash with water.Separate the organic layer,Dry with Mg2SO4,Then the solvent was removed by a rotary evaporator.The residue was purified by silica gel column chromatography,Use petroleum ether as the eluent,To obtain product 2,It is light white solid,The yield was 75%. |
| 72% |
With triphenylphosphine In toluene for 96h; Inert atmosphere; Reflux; |
1 Synthesis of compound 1-1
Under the protection ofN2, benzophenone (100 mg, 0.55 mmol) was dissolved in 10 mL of anhydrous toluene, and carbon tetrabromide (364 mg, 1.10 mmol) and triphenylphosphine (577 mg, 2.20 mmol) were added in sequence, and refluxed for 4 days .After cooling to room temperature, the reaction solution was suction filtered, and then liquid column chromatography was separated (petroleum ether) to obtain compound 1-1, a white needle-like solid of 126 mg, with a yield of 72%. |
| 64% |
With triphenylphosphine In toluene Reflux; |
|
| 64% |
With triphenylphosphine In toluene for 24h; Reflux; |
|
| 49% |
With triphenylphosphine In toluene for 72h; Inert atmosphere; Reflux; |
15
First, benzophenone is used as a raw material to synthesize dibromostilbene (yield: 49%). The synthesis scheme of the specific intermediate is as follows:Under the protection of nitrogen,Add triphenylphosphine (17.53g, 80mmol),Carbon tetrabromide (13.27g, 40mmol),Benzophenone (3.64 g) and 100 mL of toluene were placed in a 250 mL double-necked round bottom flask equipped with a reflux condenser, and the mixture was refluxed for 72 hours.The reaction mixture was cooled to room temperature and filtered to remove insoluble salts,The reaction mixture was washed three times with toluene.The filtrate was spin-dried under reduced pressure, and the intermediate was purified by silica gel column chromatography using petroleum ether as the eluent.Then, TPE-2OMe (yield: 84%) and TPE-2SMe (yield: 84%) were prepared through a cross-coupling reaction;The specific synthesis method is as follows: put dibromostilbene (0.67g, 2mmol) in a two-necked flask (100ml specification),Substituted phenylboronic acid (4mmol), Pd(PPh3)4 (115mg, 0.1mmol),Tetrabutylammonium hydrogen sulfate (68mg, 0.2mmol), K2CO3 (828mg, 6mmol),Toluene (40ml) and water (20ml),It was then heated to 90°C and reacted overnight under nitrogen protection. |
| 45% |
With triphenylphosphine In toluene at 140℃; for 96h; Inert atmosphere; |
1.1
(1) The mixture of benzophenone (1.82g, 10mmol), carbon tetrabromide (6.63g, 20mmol) and triphenylphosphine (10.5g, 40mmol) was evacuated and filled with N2 three times, and then 500mL of anhydrous toluene was added to 140 React at for 4 days. After cooling to room temperature, the mixture was filtered, washed with dichloromethane, and the filtrate was collected and washed with water. The organic layer was separated, dried with Mg2SO4, and then the solvent was removed by a rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether as the eluent to obtain product 2 as a pale white solid with a yield of 45%. |
| 35.8% |
With triphenylphosphine In toluene at 120℃; for 137h; Inert atmosphere; Schlenk technique; |
|
|
With triphenylphosphine In toluene |
|
|
With triphenylphosphine In dichloromethane at 0℃; for 1h; Inert atmosphere; |
|
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