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CAS No. : | 2398-37-0 | MDL No. : | MFCD00000081 |
Formula : | C7H7BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PLDWAJLZAAHOGG-UHFFFAOYSA-N |
M.W : | 187.03 | Pubchem ID : | 16971 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.63 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.29 cm/s |
Log Po/w (iLOGP) : | 2.29 |
Log Po/w (XLOGP3) : | 3.03 |
Log Po/w (WLOGP) : | 2.46 |
Log Po/w (MLOGP) : | 2.57 |
Log Po/w (SILICOS-IT) : | 2.52 |
Consensus Log Po/w : | 2.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.34 |
Solubility : | 0.0863 mg/ml ; 0.000461 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.89 |
Solubility : | 0.241 mg/ml ; 0.00129 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.38 |
Solubility : | 0.0783 mg/ml ; 0.000419 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H227-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
88.6% | Stage #1: With aluminum (III) chloride; magnesium In tetrahydrofuran at 50 - 55℃; Reflux |
The amount of methoxyphenylbromobenzene was increased to 243.2 g (1.3 mol), propionitrile 71.6 g (1.3 mol), the same as Example 1,The yield of methoxyphenylacetone was 88.6percent.;_In the presence of reflux condenser,The reaction flask of the dropping funnel was charged with 24.0 g (1.0 mol) of magnesium powder,Anhydrous aluminum trichloride 3.0 g,Tetrahydrofuran (THF) solution (300 mL)heating.In the dropping funnel, 187.1 g (1.0 mol) of m-methoxybenzene was slowly added,And 300 mL of tetrahydrofuran (THF)Control reaction liquid temperature 50-55 ,So that the solution has been kept in a state of slightly boiling,After the dropwise addition was heated under reflux 0.5-1.0h,To ensure that the magnesium reaction is complete,Get Grignard reagent.Stirring,55.1 g (1.0 mol) of propionitrile was slowly added to the Grignard reagent,After the dropwise addition,And then reaction 1.0-2.0h.Reaction is completed,Cold water bath slowly drop by adding 3.0mol / L hydrochloric acid,Decomposition of addition products,The inorganic phase is separated,The organic phase was subjected to atmospheric distillation to remove THF.Control the temperature to 180-185 ° C,The distillation was carried out under reduced pressure (reduced pressure at -0.095 MPa,Distillation temperature of 185 ° C),3-Methoxyphenylacetone was obtained in a yield of 78.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper(I) bromide In acetonitrile at 80℃; for 2 h; | General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: With magnesium In tetrahydrofuran for 4 h; Heating / reflux Stage #2: With water; ammonium chloride In tetrahydrofuran |
Intermediate 1 l-AUyl-3-methoxy-benzene (Ha)A solution of 3-bromoanisole (4Og, 0.2138mol) dissolved in dry THF (220 rnL) was added dropwise to a solution of magnesium (7.9g, 0.328mol) activated by pinch of iodine in dry THF (20 ml) and the reaction was shortly heated with a heat -gun to get the reaction started. After 1 hr, when the solution was gray and most of the magnesium was dissolved, allyl bromide (28.4 mL, 0.328 mol) was added. After 3 h the reaction was quenched by a saturated NH4Cl solution and the organic layer was extracted with diethyl ether. The organic phase was dried over anhydrous Na2SO4, the solvent was evaporated and the crude product was subjected to flash chromatography on silica gel (230-400 mesh) using 3-4percent ethyl acetate in petroleum ether which gave the allyl compound as yellow viscous liquid (24 g, 76percent). |
56% | With magnesium In diethyl ether at 0 - 20℃; for 2 h; Inert atmosphere | To magnesium (290 g, 12 mmol), 1-bromo-3-methoxybenzene (1 mL, 8 mmol) in Et2O (40 mL) was added dropwise under nitrogen atmosphere. The mixture was refluxed until magnesium was consumed and cooled to 0°C subsequently. To the solution allylbromide (2.4 mL, 28 mmol) was added dropwise. After stirring for 2 h at room temperature, the mixture was quenched with sat. NH4Cl aq. and extracted with ether and the subsequent purification by flash column chromatography (hexane–ethyl acetate=19 : 1) afforded 1-allyl-3-methoxybenzene (667 mg, 56percent). To a stirred solution of 1-allyl-3-methoxybenzene (667 mg, 4.5 mmol) in CH2Cl2 (60 mL), an 1 M solution of BBr3 in CH2Cl2 5.5 mL (5.5 mmol) was added dropwise at−78°C under nitrogen atmosphere. The solution was allowed to warm up to 0°C and stirred for 2 h at room temperature. The reaction mixture was quenched with water and extracted with CH2Cl2, and the subsequent purification by flash column chromatography (hexane–diethyl ether=3 : 1) afforded 3-allylphenol (302 mg, 50percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: With potassium <i>tert</i>-butylate In water at 20℃; for 0.166667 h; Inert atmosphere; Green chemistry Stage #2: With bis-(1-methylimidazole)palladium(II) dichloride In water at 100℃; for 12 h; Green chemistry |
General procedure: Under a N2 atmosphere, LiOtBu or KOtBu (3.0 mmol), H2O (2.0 mL) and acrylic acid (1.2 mmol) were added into a Schlenk reaction tube and the mixture was stirred at room temperature for 10 minutes. Then an aryl halide 2 (1.0 mmol) and Pd(II)–Im complex 1 (1.0 molpercent) were added. The mixture was stirred at 100 °C for 12 h. After cooling to room temperature, the reaction mixture was acidified by HCl (4 M) to pH 1 and extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica gel to afford the pure product 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With aluminum (III) chloride In 1,1-dichloroethane for 4 h; Heating / reflux | A dichloroethane solution (250 ml) of 1-bromo-3-methoxybenzene (30 g), acetyl chloride (15.5 g) and aluminum chloride (25.6 g) was refluxed for 4 hours. The reaction mixture was poured into ice water, and the organic layer was separated. The organic layer was washed with water, dried over magnesium sulfate and then concentrated. The residue was subjected to silica gel chromatography, and the title compound was obtained as a colorless oil (14.4 g, yield 42percent) from the diethyl ether-hexane (1:10) eluate. 1H-NMR (200MHz, CDCl3) δ: 2.61 (3H, s), 7.04 (1H, dd, J=1.9, 8.5Hz), 7.18 (1H, d, J=1.8Hz), 7.58 (1H, d, J=8.4Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | With lithium amide; N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In 1,2-dimethoxyethane at 80℃; for 24 h; | The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdCl2 (1 molpercent) in DME gave a complicated mixture of products was obtained (Table 10, Entry 1). When conducted in the presence of zinc chloride and TMEDA, however, the reaction could successfully gave the desired monoarylation product, 3-methoxyaniline, although at high concentrationsN,N-dimethyl-3-methoxyaniline was formed in a significant amount as a by- <n="62"/>product (Table 10, Entries 3 and 4). Under optimized conditions (Table 10, Entries 8 and 9), 3-methoxyaniline was formed selectively in good yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With lithium amide; zinc(II) chloride In 1,2-dimethoxyethane at 80℃; for 24 h; | The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdCl2 (1 molpercent) in DME gave a complicated mixture of products was obtained (Table 10, Entry 1). When conducted in the presence of zinc chloride and TMEDA, however, the reaction could successfully gave the desired monoarylation product, 3-methoxyaniline, although at high concentrationsN,N-dimethyl-3-methoxyaniline was formed in a significant amount as a by- <n="62"/>product (Table 10, Entries 3 and 4). Under optimized conditions (Table 10, Entries 8 and 9), 3-methoxyaniline was formed selectively in good yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere; Schlenk technique Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 16 h; Inert atmosphere; Schlenk technique |
1-bromo-3-methoxybenzene (20 g, 107 mmol) was dissolved in dry THF (200 mL) in a Schlenk tube. The solution was purged with N2 and cooled to -78 ºC. n-Butyllithium (2.5 mol/L, 64.2 mL) was added slowly. A white precipitate was formed during the addition. The mixture was stirred for 1 h at the same temperature and then trimethyl borate (74 mL, 321.0 mmol) was added. The resulting clear solution was slowly warmed to room temperature and stirred for 16 h. Concentrated hydrochloric acid was added until a pH of 3-4 was reached. The reaction mixture was poured into ethyl acetate (200 mL) and the aqueous layer was discarded. The organic layer was washed three times with saturated salt water, dried over anhydrous Na2SO4 and filtered. The solvent was removed and the product was recrystallized from ethyl acetate/petroleum ether (1:10) to afford the title compound (13.8 g, 85 percent). 1H NMR (DMSO-d6, 400 MHz, ppm): δ 8.02 (s, 2H, OH-H), 7.36 (d, J = 4.0 Hz, 2H, Ar-H), 7.25 (t, J = 8.0 Hz, 1H, Ar-H), 6.95 (d, J = 8.0 Hz, 2H, Ar-H), 3.75 (s, 3H, CH3-H); 13C NMR (CDCl3, 100 MHz, ppm): δ 158.55, 128.48, 126.32, 118.98, 115.72, 54.78. |
78% | Stage #1: With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere Stage #2: With Trimethyl borate In tetrahydrofuran; hexaneInert atmosphere |
General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 °C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 °C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 °C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.1% | With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane | 1st Stage 3-Methoxybenzeneboronic Acid 41.3 g (220 mmol) 3-bromoanisole were dissolved in 880 ml tetrahydrofuran and the solution was cooled to -70° C. in a cooling bath (ethanol/dry ice). 160 ml (250 mmol) butyllithium solution (1.6 M in hexane) were added dropwise under nitrogen such that the temperature did not rise above -60° C. After stirring at -70° C. for 1.5 hours, 75 ml (660 mmol) trimethyl borate were also added dropwise such that the temperature did not rise above -60° C. After stirring in the cold for a further hour, the mixture was warmed to 25° C. in the course of two hours, 720 ml hydrochloric acid (1 M) were added and the mixture was stirred at 25° C. for 15 hours. For working up, the mixture was extracted three times with 300 ml ether each time, the organic phases were combined, washed with 100 ml each of water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered and the filtrate was concentrated on a rotary evaporator (500-10 mbar). In this manner, 30.8 g 3-methoxybenzeneboronic acid (92.1percent of theory) were obtained. |
80% | Stage #1: With magnesium In tetrahydrofuran; toluene at 60 - 80℃; Inert atmosphere Stage #2: at 0℃; Inert atmosphere Stage #3: With sulfuric acid In tetrahydrofuran; toluene at 20℃; Inert atmosphere |
To a mixture of magnesium (2.95 g, 121mmol), THF (35mL), and toluene (35 mL)was added dropwise 3-bromoanisole 2(13.0 mL, 103mmol)with keeping temperature at 60 ºC. The reaction mixture was stirred at 80 ºC for 2hours. Prepared Grignard reagent was slowly dropwise to a toluene solution (20 mL) of trimethyl borate (11.4 mL, 102 mmol) at 0 ºC. The reaction mixture was stirred at 0 ºC for 2 hours, then neutralized with 10percent sulfuric acid, and stirred at r.t. overnight. Organic phase was separated, dried over MgSO4, and evaporated to give 3-methoxyphenylboronic acid (12.36 g, 80percent) as white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
156.1 g | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1 h; Inert atmosphere Stage #2: at 20℃; for 18 h; Inert atmosphere Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water |
n-Butyllithium in n-hexane (925.0 mL, 1.59 M) was added dropwise to a mixture of THF (1,000 mL) and 1-bromo-3-methoxybenzene (T-1) (250.0 g, 1.34 mol) at -70° C. under an atmosphere of nitrogen. After the addition had been completed, the reaction mixture was stirred at the same temperature for 1 hour. Triisopropyl borate (300.9 g, 1.60 mol) was added dropwise, and then the mixture was warmed slowly to room temperature. The stirring was continued at room temperature for 18 hours, and the reaction mixture was poured into 6M-hydrochloric acid. The mixture was extracted with ethyl acetate (500 mL) four times, and the organic layer was washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was sufficiently washed with heptane to leave colorless solids (156.1 g) of 3-methoxyphenylboronic acid (T-2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With N-Bromosuccinimide; iodine In acetonitrile for 12 h; Darkness | General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In methanol; toluene at 100℃; for 16 h; Inert atmosphere | General procedure: According to a procedure by Oxford et al.,[3] furan-2-boronic acid (168 mg, 1.5 mmol, 1.5 eq), aryl halide (1.0 mmol, 1.0 eq), Pd(PPh3)4 (116 mg, 0.1 mmol, 10 molpercent) and cesium carbonate (350 mg, 1.1 mmol, 1.1 eq) were suspended in a toluene/MeOH mixture (4:1, 10 mL). The reaction mixture was stirred for 16 h at 100 °C. The reaction mixture was diluted with EtOAc (8 mL) and the organic layer was extracted was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: With triethylsilane In dichloromethane at 0℃; for 1.16667 h; Inert atmosphere Stage #2: for 2 h; |
Friedel-Craft's Reaction Under inert atmosphere, to a solution of aluminium trichloride (1.25eq) in dichloromethane cooled at 0° C. was added the appropriate bromobenzene (1eq) drop by drop during 10 minutes. The reaction mixture was stirred at 0° C. for 1 hour then was added acyl chloride (1.05eq) in dichloromethane drop by drop. The reaction mixture was stirred for 2 hours then poured into ice. The phases were separated. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel. Example 10.1.3-Bromo-4-ethylanisole and 3-Bromo-6-ethylanisole10.1.11-(2-Bromo-4-methoxyphenyl)ethanone and 1-(4-Bromo-2-methoxyphenyl)ethanone Prepared following the Friede-Craft's method previously described (Method 10A) using 3-bromoanisole and acetyl chloride. The products were chromatographed over silica gel (elution gradient petroleum ether/ethyl acetate 98/2 to 90/10). 1-(2-bromo-4-methoxyphenyl)ethanone was obtained as a colorless oil and 1-(4-bromo-2-methoxyphenyl)ethanone was obtained as a white solid.Yield: 55percent (1-(2-bromo-4-methoxyphenyl)ethanone) and 18percent (1-(4-bromo-2-methoxyphenyl)ethanone)Rf (petroleum ether/ethyl acetate 95/5): 0.33 (1-(2-bromo-4-methoxyphenyl)ethanone) and 0.5 (1-(4-bromo-2-methoxyphenyl)ethanone)NMR 1H (CDCl3) (1-(2-bromo-4-methoxyphenyl)ethanone): 2.60 (s, 3H); 3.82 (s, 3H); 6.85 (d, 1H, J=1.9 Hz); 7.13 (s, 1H); 7.58 (d, 1H, J=5.0 Hz).NMR 1H (CDCl3) (1-(4-bromo-2-methoxyphenyl)ethanone): 2.61 (s, 3H); 3.94 (s, 3H); 7.15 (m, 2H); 7.64 (d, 1H, J=8.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: With acetic anhydride; mercury(II) oxide In dichloromethane for 0.5 h; Reflux Stage #2: With iodine In dichloromethane for 12 h; Reflux |
A stirred solution of 3-bromoanisole (10 g, 53.5 mmol), HgO (8.8 g, 40.6 mmol), Ac20 (1 mL) in CH2CI2 (100 mL) was refluxed for 30 mm. Then, 12(17.6 g, 69.5 mmol) was added by 6 portionsevery 30 mm. After refluxing for 12 h and filtration over a pad of celite, the filtrate was washed with a saturated Na2S2O3 solution. The aqueous layer was extracted with CH2CI2 (3 x 10 mL) and the combined organic layers were dried with MgSO4 and evaporated to dryness. Purification by flash chromatography (cyclohexane) afforded the titled compound.Colorless oil (yield = 94percent).1H NMR (300 MHz, CDCI3) 6 ppm 7.68 (d, J = 8.8 Hz, 1H), 7.19 (d, J = 2.8 Hz, 1H), 6.59 (dd, J = 2.8 Hz, J = 8.8 Hz, 1 H), 3.77 (s, 3H). |
35% | With iodine; silver trifluoroacetate In chloroform for 3 h; Inert atmosphere | A mixture of 3-bromophenol (0.53mmol, 1.0equiv), I2 (0.53mmol, 1.0equiv), and CF3COOAg (0.80mmol, 1.5equiv) in CHCl3 (5mL) was stirred under Ar atmosphere for 3h. The reaction was quenched with saturated Na2S2O3 (50mL) and extracted with CH2Cl2 (3×25mL). The solvent was then removed by rotary evaporation to give the brown crude oil. The crude product was purified by flash column chromatography (Hexane 100percent) to obtain product as pink oil (57mg, 35percent): Rf 0.51 (20percent EtOAc/Hexane). IR (UATR): νmax 2975, 1578, 1460, 1283, 1223, 1032, 840cm−1. 1H NMR (300MHz, CDCl3): δ 7.69 (d, J=8.7Hz, 1H), 7.20 (d, J=2.4Hz, 1H), 6.60 (dd, J=8.7, 2.1Hz, 1H), 3.78 (s, 3H); 13C NMR (75MHz, CDCl3): δ 160.1, 140.1, 129.8, 118.3, 115.3, 89.4, 55.5. EI-MS: m/z (percent) 312 (M+H+, 87), 297 (17), 172 (30), 63 (100). TOF-HRMS calcd for C7H6BrIO: 311.8641; found 311.8645, 313.8622. |