6-溴-2,3-二氢茚-1-酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: (Ethyl)triphenylphosphonium bromide (14.5 g, 39.1 mmol) was dissolved in 75 mL of tetrahydrofuran followed by addition of potassium tert-butoxide (5.29 g, 47.3 mmol) at room temperature. Upon completion of the addition, the reaction mixture was stirred for 1 hour. A solution of 6-bromo-indan-1-one 38b (3.39 g, 18.6 mmol) in 25 mL of tetrahydrofuran was added to above mixture and the mixture was stirred for another 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The reaction was quenched with 150 mL of water and then the mixture was extracted with dichloromethane (50 mL×4). The combined organic extracts were washed with saturated brine (45 mL×2), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 6-bromo-1-ethylidene-indan 41a (3.07 g, 74%) as a yellow oil. Upon completion of the addition the mixture was stirred for another 1 hour The reaction was quenched with 150 mL of water the mixture was extracted with dichloromethane (50 mL×4) The combined organic extracts were washed with saturated brine (45 mL×2) dried over anhydrous sodium sulfate filtered to remove the drying agent concentrated under reduced pressure The residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 6-Bromo-indan-1-one 38b (898 mg, 4.25 mmol) was dissolved in 5 mL of tetrahydrofuran under stirring followed by addition of above mentioned mixture. The reaction mixture was stirred at room temperature for 1 hour prior to quenching by addition of 25 mL of water. The mixture was extracted with dichloromethane (25 mL×4). The combined organic extracts were washed with saturated brine (10 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 6-bromo-1-methylene-indan 38c (830 mg, yield 93.4%) as a yellow oil. followed by addition The reaction mixture was stirred at room temperature for 1 hour to quenching by addition of 25 mL of water The mixture was extracted with dichloromethane (25 mL×4) The combined organic extracts were washed with saturated brine (10 mL×2) dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 250 mL of flask was added 3-(4-bromo-phenyl)-propionic acid 38a (20.6 g, 90 mmol, ABCR) and dried in vacuo for 20 minutes followed by addition of 110 mL of anhydrous dichloromethane under nitrogen atmosphere, and then thionyl chloride (20 mL, 276 mmol) was added. The reaction mixture was heated to reflux overnight. The mixture was concentrated under reduced pressure to remove most solvent followed by addition of 100 mL of dichloromethane, and then aluminium trichloride (24.5 g, 25.8 mmol) was added. The generated gas was released. The mixture was warmed up to reflux and stirred overnight. The mixture was poured into 200 g of ice to form a copious amount of precipitates and filtered through silica gel. The filtrate was separated and the aqueous layer was extracted with 30 mL of dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound 6-bromo-indan-1-one 38b (18.34 g, yield 96.6%) as a yellow solid. dried in vacuo for 20 minutes followed by addition of 110 mL of anhydrous dichloromethane under nitrogen atmosphere The reaction mixture was heated to reflux overnight The mixture was concentrated under reduced pressure to remove most solvent followed by addition of 100 mL of dichloromethane The mixture was warmed up to reflux to form a copious amount of precipitates filtered through silica gel The filtrate was separated the aqueous layer was extracted with 30 mL of dichloromethane The combined organic extracts were dried over anhydrous magnesium sulfate concentrated under reduced pressure

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 6-bromoindan-1-one (1 eq.) and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (1.3 eq.) in DMF (0.1 M) was added trans-bis(triphenylphosphine) palladium(II) bromide (0.05 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 M aq. Na2CO3 (3 eq.) was added and the resulting mixture was stirred at 100° C. for 1 h. The now black suspension was cooled to RT, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a beige solid. The vessel was repeatedly evacuated back-filled with nitrogen The now black suspension was cooled to RT extracted with ethyl acetate The combined organic extracts were washed with water and brine dried over Na2SO4 filtered the filtrate concentrated in vacuo Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 6-bromo-2,3-dihydro-1H-inden-1-one (0.3 g, 1.36 mmol), paraformaldehyde (0.4 g, 13.6 mmol), phenylboronic acid (0.2 g, 1.64 mmol) and trifluoroacetic acid (0.1 mL, 0.15 g, 1.36 mmol) in dry toluene (10 mL) was refluxed for 5 hours. When starting material was totally consumed, the crude mixture was cooled to room temperature, neutralized with saturated aqueous Na2CO3, extracted with ethyl acetate, dried and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, petroleum ether-ethyl acetate, 95:5) to give compound 6-bromo-2-methylene-2,3-dihydro-1H-inden-1-one (89 mg, 30%) as a white solid. 1H NMR (CDCl3, 400 MHz): 3.71 (s, 2H), 5.68 (s, 1H), 6.39 (s, 1H), 7.38-7.40 (d, 1H), 7.70-7.72 (d, 1H), 7.99 (s, 1H). was totally consumed extracted with ethyl acetate dried concentrated under reduced pressure The residue was purified by flash column chromatography (silica gel, petroleum ether-ethyl acetate, 95:5)