| 85% |
With hydrogenchloride; mercury dichloride; zinc In ethanol; water for 8h; Reflux; |
3.1
877mg of zinc powder, 405mg of mercuric chloride, 20ml of concentrated hydrochloric acid, and 40ml of water were mixed and stirred for 5min then left to stand. To the solution was added 40ml 95% ethanol and 2.33g 3-bromo-9-fluorenone then refluxed for 8h. During the reaction 30ml of concentrated hydrochloric acid was added portionwise. It was cooled and filtered. The crude product was recrystallized from ethanol and dried to give a white solid product, 3-bromo-substituted fluorene 1.87g, 85% yield. |
| 85% |
With hydrogenchloride; mercury dichloride; zinc In ethanol; water for 8h; Reflux; |
3.4 4) Synthesis of 3-bromo-substituted fluorene
The mixture was stirred zinc 877mg, 405mg mercuric chloride, 20ml of concentrated hydrochloric acid and 40ml water 5min, standing. Water was decanted, added 40ml95% ethanol was added 2.33g3- bromo-9-fluorenone, the reaction was refluxed for 8h, the reaction 30ml of concentrated hydrochloric acid was added portionwise, stiff finished, cooled, suction filtered, the crude product from ethanol crystals, and dried to give a white solid product, 3-bromo-substituted fluorene 1.87 g, yield 85% |
| 85% |
With hydrogenchloride; mercury dichloride; zinc In ethanol; water for 8h; Reflux; |
3.1
Mix 877 mg of zinc powder, 405 mg of mercuric chloride, 20 ml of concentrated hydrochloric acid and 40 ml of water for 5 mm, add 40 ml of 95% ethanol, add 2.33 g 3-bromo-9-fluorenone, reflux reaction 8 h, the reaction process by adding 30 ml of concentrated hydrochloric acid, hardened, cooled, The product was recrystallized from ethanol and dried to give 1.87 g of 3-bromo-substituted fluorene as a white solid in 85% yield. Feature: ‘H NMR (CHC13 d3) öppm:8.01 (s, 1H, Aromatic ring H)7.87(m,1H, Aromatic ring H), 7.55(s, 1H, Aromatic ring H), 7.45(m, 2H, Aromatic ring H), 7.38(m, 1H, Aromatic ring H), 7.28(m, 1H, Aromatic ring H),4.12(m, 2H, CH2). A 3-bromofluorene solid (1.87 g) was dissolved in 50 ml of anhydrous tetrahydrothran. 1.1 equivalents of magnesium powder and 200 mg of catalyst were added and the temperature was raised. After the reaction was initiated, the reaction was continued for 2 hours and then cooled to obtain a reagent in tetrahydrofuran solution. Cool to the internal temperature of 0° C.-5° C., and then drop the solution of ethyl bromide. After completion of the dropwise addition, the temperature was raised to room temperature for 4 hours. TEC showed that the reaction was complete. Slowly add an aqueous solution of ammonium chloride to quench the reaction. And extracted three times with 25 ml of ethyl acetate to combine the organic phases. The organic phase was dried with a desiccant and the desiccant was removed by filtration. Evaporated to dryness. The crude product was recrystallized from ethyl acetate and petroleum ethet To give a white 3-ethylfluorene solid (889 mg, 60%). |
| 55.4% |
Stage #1: 3-bromofluoren-9-one With hydrazine hydrate In diethylene glycol at 80 - 100℃; for 5h;
Stage #2: With potassium hydroxide In water; diethylene glycol at 120℃; for 1h; |
|
|
With hydrogenchloride; mercury; zinc |
|
| 70 mmol |
With triethylsilane; trifluoroacetic acid at 20℃; |
1.5
(5) take vii 100mmol, adding solvent trifluoroacetic acid, triethyl silane 300mmol,The mixture was stirred at room temperature overnight, and after completion of the reaction, the reaction solution was poured into water,Extracted with EA three times, washed with aqueous NaOH solution,Dried and concentrated to give 70 mmol of product. |
|
With hydrazine hydrate In ethanol; toluene for 2h; Reflux; |
17.2 Step 2
To 49 ml (1000 mmol) of hydrazine hydrate was added 3 g of Raney nickel,A solution of 64 g (250 mmol) of 3-bromofluorenone,1000 ml of toluene and 2000 ml of ethanol,Fast stirring, reflux reaction 2 hours,After the completion of the reaction,The resulting crude product was passed through a silica gel column to give the product 17-0, 37 g. |
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