Structure of 25032-74-0
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| CAS No. : | 25032-74-0 |
| Formula : | C13H8Br2O |
| M.W : | 340.01 |
| SMILES Code : | O=C(C1=CC=CC(Br)=C1)C2=CC=CC(Br)=C2 |
| MDL No. : | MFCD00458551 |
| InChI Key : | QBNTVYGGZGPJDZ-UHFFFAOYSA-N |
| Pubchem ID : | 12731928 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 16 |
| Num. arom. heavy atoms | 12 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 71.72 |
| TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.88 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.82 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.44 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.3 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.73 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.23 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-5.41 |
| Solubility | 0.00133 mg/ml ; 0.00000391 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-4.91 |
| Solubility | 0.00417 mg/ml ; 0.0000123 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.53 |
| Solubility | 0.0000994 mg/ml ; 0.000000292 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.95 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.74 |
* 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 |
|---|---|---|
| 88% | With pyridinium chlorochromate; In dichloromethane; for 1.5h;Molecular sieve; | Next, 200 mL Erlenmeyer flask was charged with Celite8.5 g,3.4 g of active molecular sieves 3A, 60 ml of dichloromethane,2.72 g (12.6 mmol) of pyridinium chlorochromate was added and stirred.Compound h 1.44 g (4.21 mmol) of dichloromethane 10 mlAfter adding the solution, the mixture was stirred for 1.5 hours. For the reaction mixture,The insoluble portion was removed with an alumina short column. After concentration of the filtrate,The obtained viscous substance was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to obtain 1.26 g (3.71 mmol) of the target compound i,Obtained in 88% yield. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.5h; | A mixture of pyridiniumchlofochromate (2.72 g, 12.6 mmol) in dichloromethane (60 mL) was added a solution of 3,3'-Dibromophenylmethanol in dichloromethane (10 mL). The resulting mixture was stirred 1.5 h at room temperature. The organic layer was concentrated under reduced pressure and the crude product purified by silica gel column chromatography (hexane:ethylacetate = 9:1) to give 2 as a pale yellow solid. (1.26 g, 88%). |
| 85% | With pyridinium chlorochromate; In dichloromethane; at 0 - 20℃; for 5.66667h; | Bis(3-bromophenyl) ketone. 30 mL of anhydrous CH2Cl2 were poured into a flask containing PCC (1.92 g, 8.73 mmol) and celite (1.9 g). The suspension was stirred at 0 C. under nitrogen for 10 minutes, at which point, 10 mL of a CH2Cl2 solution of the appropriate alcohol (1.99 g, 5.82 mmol) were added. After the reaction was stirred at room temperature for 5.5 h, 15 mL of Et2O were added and the reaction mixture was filtered through fluorisil-silica gel and rinsed with extra Et2O (10 mL). The organic phase was dried under Na2SO4 and the solvent was evaporated to afford 1.673 g (4.92 mmol) of pure product in a 85% yield.1H NMR (300 MHz, CDCl3, δ): 7.92 (t, J=1.8, ArH, 2H), 7.73 (ddd, J=8.0, 2.0, 1.1, ArH, 2H), 7.68 (ddd, J=7.7, 1.6, 1.2, ArH, 2H), 7.37 (t, J=7.8, ArH, 2H).13C NMR (75 MHz, CDCl3): δ 193.7, 138.8, 135.7, 132.7, 130.0, 128.5, 122.8. |
| 76.8% | With pyridinium chlorochromate; In dichloromethane; at 20℃; for 12h; | In a 5 L round bottom flask, 150 mL of methylene chloride was added to 10 g (0.05 mol) of the compound represented by the formula [1-b] obtained from the scheme 2, and pyridinium chlorochromate25.7 g was dissolved in 200 mL of methylene chloride and added to the reaction.The mixture was stirred at room temperature for 12 hours. After completion of the reaction, 900 mL of ethanol was added and stirred, followed by filtration. The organic layer was concentrated under reduced pressure and then dried to obtain 7.6 g (76.8%) of a compound represented by the formula 1-c |
| 72% | With dipyridinium dichromate; In dichloromethane; at 0 - 25℃; for 3h; | The product obtained in step (1) was added to dry dichloromethane (DCM) (75mL), dissolved at room temperature with stirring, then cooled to 0C, and pyridinium dichromate (PDC) (12.4g, 32.96) was slowly added. mmol), the reaction mixture was stirred at room temperature for 3 hours.At the end of the reaction, H2O and ethyl acetate (EA) (the mass ratio ofH2O: EA is 1:1) are added for extraction, the organic phases are combined, dried with anhydrous Na2SO4,and then removed by a rotary evaporator. The solvent was removed to obtain the crude product.The crude product was purified by column chromatography (silica gel column, eluent PE:EA=50:1, volume ratio) to obtain a white powder as the product with a yield of 72%. |
| With manganese(IV) oxide; In dichloromethane; at 20℃; for 1h; | Under a nitrogen atomosphere, a tetrahydrofuran solution (10 mL) of 1,3-dibromobenzene (1.9 mL, 16.1 mmol) was cooled to -70 C. and then n-butyllithium (10.0 mL, 1.60 N, 16.1 mmol) was added dropwise thereto over a period of 15 minutes. After the mixture was stirred at -70 C. additionally for 20 minutes, a tetrahydrofuran (10 mL) solution of 3-bromobenzaldehyde (1.7 mL, 14.6 mmol) was added dropwise over a period of 15 minutes, and the mixture after the dropwise addition was allowed to warm to room temperature. The reaction solution was poured into aqueous ammonium chloride-saturated solution, and the mixture was extracted with toluene. The organic phases obtained were combined and concentrated to give 1,1-bis(3-bromophenyl)methanol as a colorless oily substance. The substance was used in the next reaction without further purification. Manganese dioxide (14.2 g, 146.0 mmol) was added to a methylene chloride (70 mL) solution of 1,1-bis(3-bromophenyl)methanol (14.6 mmol) and the mixture was stirred at room temperature in air for 1 hour. The reaction solution was filtered. The filtrate was concentrated and the residue obtained was purified by silica gel column chromatography and recrystallization to give 3,3'-dibromobenzophenone as white powder (3.5 g). Yield: 70.5%. 1H-NMR (200 MHz, CDCl3) δ: 7.38 (t, J=8.0 Hz, 2H), 7.65-7.79 (m, 4H), and 7.93 (dd, J=1.6, 2.0 Hz, 2H). |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 18% | Bis(3-bromophenyl) ketone thiosemicarbazone (14) Into a round bottom flask containing the appropriate ketone (1.044 g, 3.07 mmol), 35 mL of anhydrous methanol were added and the solution was refluxed for about 15 minutes. To the warm ketone solution, thiosemicarbazide (0.294 g, 3.23 mmol) and 1% solution of HOAc (1.5 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 46 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (20% EtOAc/80% hex) to obtain 0.231 g (0.559 mmol) of the product in an 18% yield.1H NMR (360 MHz, CDCl3, δ): 8.59 (br s, NH, 1H), 7.72 (s, ArH, 2H), 7.41 (m, ArH, 6H), 6.92 (br s, NH2, 1H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75.8% | In a nitrogen atmosphere, a n-pentane solution of t-butyllithium (17.8 ml, 1.60M, 28.5 mmol) was dropwise added to tetrahydrofuran cooled to -70C, then a tetrahydrofuran (5 ml) solution of 2-bromopyridine (1.2 ml, 12.9 mmol) was added thereto while 15 minutes, after a dropwise, the mixture was stirred at -70C for 30 minutes. Then, a tetrahydrofuran solution of zinc chloride (31.8 ml, 0.50 M, 15.9 mmol) was added to the mixture while 10 minutes. Thereafter, the temperature of the reaction mixture was allowed to warm to room temperature while 1 hour, tetrakis(triphenylphosphine)palladium (203 mg) and <strong>[25032-74-0]3,3'-dibromobenzophenone</strong> (2.0 g, 5.88 mmol) were successively added thereto, the reaction mixture was stirred under reflux for 18 hours. After the reaction mixture was allowed to cool, then the mixture was poured into a mixture of ethylenediaminetetraacetic acid (7.0 g)/an aqueous saturated sodium hydrogen carbonate solution (210 ml), an organic layer was separated, furthermore an aqueous layer was extracted with toluene. The organic layer was combined, and the solvent was distilled off, and the residue was purified by silica gel column chromatography and recrystallization, thereby obtaining 1.5 g of carbonylbis[3-(2-pyridyl)benzene as white powder. Yield: 75.8%. 1H-NMR (CDCl3)δ: 7.22-7.34(m, 2H), 7.62(dt, J=0.4, 7.8Hz, 2H), 7.74-7.84(m, 4H), 7.88(dt, J=7.8, 1.4HZ, 2H), 8.30(ddd, J=1.4, 1.8, 7.6Hz, 2H), 8.45(t, J=1.6Hz, 2H), 8.71(dt, J=4.4, 1.6HZ, 2H) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 2.2 g (78.6%) | With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; | EXAMPLE 37 A suspension of methyltriphenylphosphonium bromide (3.25 g; 9.05 mmol) in 100 ml of ether was added at 0 C. n-butyllithium in hexane (3.7 ml; 9.05 mmol) and the mixture was allowed to stir at room temperature for 1 h. To the above mixture was added 2.8 g (8.2 mmol) of 1,1-di(m-bromophenyl)ketone in 30 ml of tetrahydrofuran and the mixture was stirred for 10 min. The above reaction mixture was quenched with acetone (5 ml), stirred for 5 minutes, filtered, and the filtrate was concentrated in vacuo. The residue in hexane/methylene chloride (3:1) was purified by chromatography on silica eluding with hexane to afford 2.2 g (78.6%) of 1,1-di(m-bromophenyl)ethylene (Formula III: R2 =R3 =H;R4 =R5 =3-Br-phenyl). |
| 2.2 g (78.6%) | With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; | (a) To a suspension of methyltriphenylphosphonium bromide (3.25 g; 9.05 mmol) in 100 mL of ether was added at 0 C. n-butyllithium in hexane (3.7 mL; 9.05 mmol) and the mixture was heated to stir at room temperature for 1 h. To the above mixture was added 2.8 g (8.2 mmol) of 1,1-di(m-bromophenyl)ketone in 30 mL of tetrahydrofuran and the mixture was stirred for 10 min. The above reaction mixture was quenched with acetone (5 mL), stirred for 5 minutes, filtered, and the filtrate was concentrated in vacuo. The residue in hexane/methylene chloride (3:1) was purified by chromatography on silica eluding with hexane to afford 2.2 g (78.6%) of 1,1-di(m-bromophenyl)ethylene (Formula III: R3 =R4 =H; R5 =R6 =3--Br-phenyl). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64.9% | With (E)-2-hydroxylbenzaldehyde oxime; caesium carbonate;copper(I) oxide; In acetonitrile; for 24h;Heating / reflux; | A mixture of <strong>[25032-74-0]3,3'-dibromobenzophenone</strong> (3.0 g, 8.8 mmol), pyrazole (1.5 g, 22.1 mmol), cesium carbonate (8.6 g, 26.5 mmol), cuprous oxide (126 mg), salicylaldoxime (484 mg) and acetonitrile (20 mL) was stirred in reflux condition under nitrogen atmosphere for 24 hours. The reaction solution obtained was allowed to cool to room temperature. Water and toluene were added thereto and the extraction was carried out. The organic phases obtained were combined and concentrated. The residue obtained was purified by silica gel column chromatography and recrystallization to give carbonyl bis[3-(1-pyrazolyl)benzene] as white powder (1.8 g). Yield: 64.9%. 1H-NMR (200 MHz, CDCl3) δ: 6.51 (dt, J=0.6, 1.8 Hz, 2H), 7.60 (t, J=7.7 Hz, 2H), 7.68-7.78 (m, 4H), 7.98-8.08 (m, 4H), and 8.12-8.18 (m, 2H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen bromide; magnesium; In tetrahydrofuran; acetic acid; toluene; | A) 9,9-Bis(3-bromophenyl)-9H-fluorene 62.9 g (270 mmol) of 2-bromobiphenyl mixed with 400 ml of THF, 550 ml of toluene, 45 ml of 1,2-dimethoxyethane and 2.6 ml of 1,2-dibromoethane are reacted with 6.6 g (250 mmol) of magnesium to give the corresponding Grignard compound. A solution of 60.0 g (176 mmol) of bis(3-bromophenyl) ketone in 600 ml of THF is added dropwise to the cooled Grignard solution. When the addition is complete, the reaction mixture is heated under reflux for 4 h, the solvent is then removed in vacuo, the residue is dissolved in 700 ml of glacial acetic acid, 10 ml of hydrogen bromide in 30% glacial acetic acid are added, and the mixture is heated under reflux for 6 h. After cooling with stirring, the precipitated solid is filtered off with suction, washed twice with 200 ml of glacial acetic acid each time and three times with 300 ml of ethanol each time and then dried in vacuo. Yield: 69.0 g (145 mmol), 82.1%, 99% pure according to 1H-NMR. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 77% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water; for 12h;Inert atmosphere; Reflux; | A mixture of 3,3'-Dibromobenzophenone (386 mg, 1.14 mmol), 9-phenylcarbazol-3-bronic acid (800 mg, 2.78 mmol), 1.35 M potassium phosphate aq. (10 mL), xylene (20 mL) and ethanol (10 mL) was deoxygenated with nitrogen for 60 min. 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (66 mg,0.16 mmol) and tris(dibenzylideneacetone) dipalladium(0) (73 mg, 0.08 mmol) was added. The reaction mixture was refluxed for 12 h. After cooling to room temperature, water was added. The aqueous layer was extracted with toluene. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (hexane:ethylacetate = 4:1 to 3:2) to give BCzBP as a white solid (584 mg, 77%). 1H NMR (400 MHz, DMSO) δ [ppm]: 8.65 (s, 2H), 8.30 (d, J = 8 Hz,2H), 8.21 (s, 2H), 8.13 (d, J = 8 Hz, 2H), 7.83-7.78 (m, 4H), 7.74-7.62 (m, 10H), 7.55 (t, J = 7 Hz,2H), 7.49-7.36 (m, 6H), 7.26 (t, J = 7 Hz, 2H). 13C NMR (400 MHz, CDCl ) δ [ppm]: 197.07, 3142.19, 141.32, 140.54, 138.20, 137.45, 132.22, 131.29, 129.92, 128.82, 128.77, 128.38, 127.57, 127.02, 126.24, 125.36, 123.93, 123.27, 120.41, 120.15, 118.98, 110.16, 109.92. Elemental anal.Calcd for C49H32N2O: C, 88.53; H, 4.85; N, 4.21. Found: C, 88.66; H, 4.84; N, 4.16. EI-MS (m/z):[M+H]+ calcd for C49H32N2O, 664; found, 666. Purity (determined by HPLC): 99.9%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 42% | A 300 mL three-necked flask was charged with 1.21 ml (9.96 mmol) of the compound f,150 ml of dehydrated diethyl ether was added, and under a nitrogen atmosphereAnd the mixture was stirred at -70 C. or lower. N-Butyl lithium 6.0 ml (1.65 mol / l n-hexane solution,9.90 mmol) was added at -70 C. or less within 60 minutes, and the mixture was stirred for 2 hours.A solution of 0.29 ml (11.0 mmol) of compound g in 30 ml of dehydrated diethyl etherThe solution was added all at once and then stirred for a further 2 hours. After returning the reaction mixture to room temperature,100 ml of methanol was added to terminate the reaction. After distilling off the solvent,The obtained viscous substance was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to obtain 1.44 g (4.21 mmol) of the objective compound h,It was obtained in a yield of 42%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 76% | 1,3- dibromobenzenes (59.0 g, 250 mmol) aredissolved among the diethylether of 1.1 l and it cools to -65.The n-BuLi solution (2.5 M among the n-hexane) of 100 ml is dipped as thegradually and the mixture is stirred for the additional 1 hour. The N,N-dimethylcarbamoyl chloride is added under the fierce mixingat a time. In -65 the mixture, it heats to the gradually for 1 hourafter doing the mixing. Subsequently, the mixture of the acetic acid of thewater of 250 ml and 25 ml are dipped as the gradually. The product isprecipitated as the white solid. Solid is filtered to the suction andit rinses in fresh water after washing to water and ethanol. The yield is 42.2 g(76% of the Theoretical value) as the white solid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62% | First, magnesiums (3.17 g, 120.6 mmol) areintroduced to the flask including one iodine crystal. First, 1- bromo -2-phenoxy benzenes (23.2 g, 93.2 mmol), the anhydrous tetrahydrofuran of 190 ml,and 1,2- dimethoxyethane of 26 ml and 1,2- dichloroethane of 0.78 ml areintroduced to the dropping funnel. The outbound - material blend is dipped asthe gradually. In 70 the reactant, it cools for the additional 3 hoursafter doing the mixing. Bis (3- bromophenyl) methanones (32 g, 93.2 mmol) aredissolved among THF of 200 ml and it dips as the gradually. The reactant isstirred under the reflux for 4 hours. Subsequently, the arrangement is filteredand THF is removed of the Rotavapor. The acetic acid of 400 ml and concentratedhydrochloric acid of 75 ml are added and the water of 200 ml the mixture isadded in 75for 4 hours after doing the mixing. The solid in which the colour is pale isfiltered to the suction and it washes to the methanol. Solid is stirred for1 hour among the boiling ethyl acetate and it filters and it washes to ethanol.The yield is 28.2 g (62% of the Theoretical value) as the white solid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | Firstly, magnesiums (6.73 g, 255.8 mmol) areintroduced to the flask including one iodine crystal. 2- bromo biphenyls (64.4g, 276.3 mmol), the anhydrous tetrahydrofuran of 400 ml, the anhydrous tolueneof 500 ml, and 1,2- dimethoxyethane of 45 ml and 1,2- dichloroethane of 2.65 mlare introduced within the dropping funnel. The outbound - material blend isdipped as the gradually. The reactant is cooled under the reflux for theadditional 1 hour after doing the mixing. Bis - (3- bromo-phenyl) methanones(61.4 g, 180.6 mmol) are dissolved among THF of 600 ml and it dips as thegradually. The reactant is stirred under the reflux for 5 hours. Thearrangement is filtered and THF is evaporated in the Rotavapor. The acetic acidof 500 ml, and the acetic acid of 200 ml and HBr of 10 ml are added and themixture is stirred under the reflux for 64 hours. The solid in which the colouris pale is filtered to the suction and it washes to the ethyl acetate andethanol. The yield is 79.8 g (92% of the Theoretical value) as the white solid | |
| 91% | About 10 ml of a solution of 2-bromobiphenyl (80.0 g, 343 mmol) and 1,2-dibromoethane (3.6 ml, 43 mmol) in a mixture of 640 ml of toluene, 520 mlof tetrahydrofuran and 60 ml of ethylene glycol dimethyl ether are added to8.8 g of magnesium (334 mmol) and heated. After onset of the reaction,the heating is removed and the remaining solution is added dropwise insuch a way that reflux is maintained. On completion of addition, the mixtureis heated to reflux for 1 h. Subsequently, under gentle reflux, a solution ofthe ketone KI (80.0 g, 235 mmol) in 800 ml of tetrahydrofuran is addeddropwise and the mixture is stirred under reflux for 5 h. The heating isremoved and the mixture is stirred for 14 h. The solvents are removedcompletely on a rotary evapourator. The remaining residue is taken up in amixture of 920 ml of glacial acetic acid and 13.2 ml of a 33% solution of hydrogen bromide in acetic acid, and heated to reflux for 6 h. After removing the heating, the mixture is stirred for 16 h. The solid material formed is filtered off with suction, washed with about 150 ml of glacial acetic acid and three times with 250 ml each time of ethanol and then dried in a vacuum drying cabinet. This leaves 101.6 g (213 mmol, 91% of theory)of the product as a light grey solid having a purity of about 99% by 1 HNMR. | |
| 82.1% | 62.9 g (270 mmol) of 2-bromobiphenyl mixed with 400 ml of THF, 550 ml of toluene, 45 ml of 1,2-dimethoxyethane and 2.6 ml of 1,2-dibromoethane are reacted with 6.6 g (250 mmol) of magnesium to give the corresponding Grignard compound. A solution of 60.0 g (176 mmol) of bis(3-bromophenyl) ketone in 600 ml of THF is added dropwise to the cooled Grignard solution. When the addition is complete, the reaction mixture is heated under reflux for 4 h, the solvent is then removed in vacuo, the residue is dissolved in 700 ml of glacial acetic acid, 10 ml of hydrogen bromide in 30% glacial acetic acid are added, and the mixture is heated under reflux for 6 h. After cooling with stirring, the precipitated solid is filtered off with suction, washed twice with 200 ml of glacial acetic acid each time and three times with 300 ml of ethanol each time and then dried in vacuo. Yield: 69.0 g (145 mmol), 82.1%, 99% pure according to1H-NMR. |
[ 25032-74-0 ]
[ 3508-62-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 35% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 24h; | Well-dried 100 mL three-necked round bottom flask charged with bis (3-bromophenyl) methanone (1 g, 2.94 mmol), 10,10-diphenyl-5,10-dihydrodibenzo [b, e] [1,4] azasiline (2.26 g, 6.47 mmol), Na-t-butxide (0.57 g, 5.9mmol), tris (tertbutyl) phosphine (0.06 g, 0.29 mmol) And Pd2(dba)3 (0.13 g, 0.15 mmol) were dissolved in 15 ml of toluene and it was stirred for 24 hours at 110C . After completion of the reaction was poured into water, and extracted three times with chloroform. The extracted organic layer was dried using MgSO4, the solvent was removed using a rotary evaporator, and separated by column chromatography using EA / n-Hexane (1/3) to obtain the compound 2 g (yield = 35%). |

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