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Chemical Structure| 1515-88-4 Chemical Structure| 1515-88-4

Structure of 1515-88-4

Chemical Structure| 1515-88-4

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Product Details of [ 1515-88-4 ]

CAS No. :1515-88-4
Formula : C8H9BrO
M.W : 201.06
SMILES Code : COCC1=CC=C(Br)C=C1
English Name :1-Bromo-4-(methoxymethyl)benzene
MDL No. :MFCD09265134
InChI Key :JIMMXGXOJQXOQA-UHFFFAOYSA-N
Pubchem ID :12662296

Safety of [ 1515-88-4 ]

Application In Synthesis of [ 1515-88-4 ]

* 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.

  • Downstream synthetic route of [ 1515-88-4 ]

[ 1515-88-4 ] Synthesis Path-Downstream   1~14

  • 1
  • [ CAS Unavailable ]
  • [ 589-15-1 ]
  • [ 1515-88-4 ]
YieldReaction ConditionsOperation in experiment
96% In methanol at 40℃; for 2h; Heating / reflux; 14 Description 14: (4-Bromophenyl)methyl methyl ether; In a 2000ml pear flask 1-bromo-4-(bromomethyl)benzene (142.2 g, 569 mmol) was treated with methanol (580 ml) to give a colourless suspension. Sodium methoxide (35.6 g, 626 mmol) was then added portionwise. The reaction was slightly exothermic and at the end of the addition a clear solution was observed and the internal temperature rose to 400C. After the exothermic phase the reaction was refluxed for 2h then the mixture was cooled to room temperature, concentrated under vacuum and finally partitioned between 2500 ml of ethyl acetate and 1000 ml of water. The organic phase was washed with 2 x 500ml of water, then 500 ml of brine and finally dried over anhydrous sodium sulphate. The organic was evaporated under vacuum to obtain the title product as a colourless oil (110.6g; 96%). 1H NMR (CDCI3) δ: 3.40 (3H,s) , 4.41 (2H, s), 7.20 (2H, d), 7.50 (2H, d).
With methanol
  • 2
  • [ 873-75-6 ]
  • [ 74-88-4 ]
  • [ 1515-88-4 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 4-Bromobenzyl alcohol With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; paraffin oil at 20℃; for 15h;
99% Stage #1: 4-Bromobenzyl alcohol With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #2: methyl iodide In dimethyl sulfoxide for 0.166667h; 2.2-1 Step 2-1:
Synthesis of 1-bromo-4-(methoxymethyl)benzene DMSO (117 mL)/KOH (214 mmol, 12 g) was added to a flask, and 4-bromobenzyl alcohol (53.5 mmol, 10.0 g) was added and then stirred at room temperature for 1 hour. MeI (107 mmol, 6.6 mL) was added to the reaction product and then stirred for 10 minutes. After the reaction was completed, the reaction mixture was poured into H2O and then extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4 and then vacuum dried to obtain 1-bromo-4-methoxymethyl benzene (10.6 g, 99%). 1H NMR (500 MHz, CDCl3, 7.24 ppm): 3.41 (3H, s), 4.39 (2H, s), 7.11-7.53 (4H, m)
96% With potassium hydroxide In dimethyl sulfoxide for 0.5h; Ambient temperature;
93% With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane for 3h;
88.4% Stage #1: 4-Bromobenzyl alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 3h; V.3.1 Synthesis of 1-bromo-4-(methoxymethyl)benzene [5.3a]. NaH (60%) (0.51g, 21.4 mmoi, 2.0 equiv) was dissoived in THE (50 mL) and cooied to 0 °C. (4-bromophenyi) methanoi (2 g, 10.7 mmoi, 1.0 equiv) in THE (5 mL) was added drop wise and the reaction mixture was stirred at room temperature for 1 hour. A soiution iodomethane (1.82 g, 12.8 mmoi,1.2 equiv) in THE (5 mL) was added at 0 °C and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic iayer was washed with brine, dried over sodium suifate and concentrated to afford product 5.3a (1.9 g, 88.4 % yieid). 1H NMR (400 MHz, DMSO) 6 7.60- 7.50 (m, 2H), 7.28 (d, J = 8.4 Hz, 2H), 4.44 - 4.32 (m, 2H), 3.29 (s, 3H).
87% With potassium <i>tert</i>-butylate In tetrahydrofuran
61% With sodium hydride In tetrahydrofuran for 2h; Ambient temperature;
In N,N-dimethyl-formamide 41 EXAMPLE 41 EXAMPLE 41 This Example illustrates the preparation of 4-bromobenzyl methyl ether. 4-Bromobenzyl alcohol (1.87 g) was added over 10 minutes to a stirred suspension of sodium hydride (0.24 g--used directly in the form of 0.48 g of a 50% dispersion in oil) in dry N,N-dimethylformamide (10 cm3) under an atmosphere of nitrogen. Afer evolution of hydrogen had ceased (20 minutes), methyl iodide (1.42 g) was added and the reaction mixture was stirred for a further 10 minutes. The mixture was poured into water and the organic layer separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried over anhydrous sodium sulphate, and concentrated by evaporation under reduced pressure. The residual, crude product was purified by column chromatography on a silica gel support, eluding with n-hexane containing 12.5% by volume ethyl acetate, to give 4-bromobenzyl methyl ether (1.6 g). 1 H NMR (CDCl3) (ppm):3.44 (3H,s); 4.46 (2H,s); ca. 7.3 (4H,ABq)
In N,N-dimethyl-formamide 40 EXAMPLE 40 EXAMPLE 40 This Example illustrates the preparation of 4-bromobenzyl methyl ether. 4-Bromobenzyl alcohol (1.87 g) was added over 10 minutes to a stirred suspension of sodium hydride (0.24 g--used directly in the form of 0.48 g of a 50% dispersion in oil) in dry N,N-dimethylformamide (10 cm3) under an atmosphere of nitrogen. Afer evolution of hydrogen had ceased (20 minutes), methyl iodide (1.42 g) was added and the reaction mixture was stirred for a further 10 minutes. The mixture was poured into water and the organic layer separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried over anhydrous sodium sulphate, and concentrated by evaporation under reduced pressure. The residual, crude product was purified by column chromatography on a silica gel support, eluding with n-hexane containing 12.5% by volume ethyl acetate, to give 4-bromobenzyl methyl ether (1.6 g). 1 H NMR (CDCl3) δ (ppm): 3.44 (3H, s); 4.46 (2H, s); ca. 7.3 (4H, ABq)
In N,N-dimethyl-formamide 40 EXAMPLE 40 EXAMPLE 40 This Example illustrates the preparation of 4-bromobenzyl methyl ether. 4-Bromobenzyl alcohol (l.87g) was added over l0 minutes to a stirred suspension of sodium hydride (0.24g - used directly in the form of 0.48g of a 50% dispersion in oil) in dry N,N-dimethylformamide (l0 cm3) under an atmosphere of nitrogen. Afer evolution of hydrogen had ceased (20 minutes), methyl iodide (l.42g) was added and the reaction mixture was stirred for a further l0 minutes. The mixture was poured into water and the organic layer separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried over anhydrous sodium sulphate, and concentrated by evaporation under reduced pressure. The residual, crude product was purified by column chromatography on a silica gel support, eluding with n-hexane containing l2.5% by volume ethyl acetate, to give 4-bromobenzyl methyl ether (l.6g). 1H NMR (CDCl3) δ (ppm): 3.44 (3H,s); 4.46 (2H,s); ca. 7.3 (4H,ABq)
In tetrahydrofuran; water R.97 Reference Example 97 Reference Example 97 In THF (200 ml) was dissolved 4-bromobenzyl alcohol (19.8 g), and to the solution was added under ice-cooling 65% sodium hydride (3.6 g). The mixture was stirred at room temperature for 30 minutes, and to the mixture was added dropwise under ice-cooling iodomethane (8.0 ml). The mixture was stirred at room temperature for 2 hours. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1) to give 1-bromo-4-(methoxymethyl)benzene (14.8 g).
90% With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;

  • 3
  • [ 3553-80-8 ]
  • [ 1515-88-4 ]
  • [ 90021-26-4 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 1-bromo-4-methoxymethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: ethyl N,N-diethylcarbamate In tetrahydrofuran; hexane at -78℃; for 0.416667h;
  • 4
  • [ 1515-88-4 ]
  • [ 126200-19-9 ]
  • [ 1005487-24-0 ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: 1-bromo-4-methoxymethylbenzene With magnesium In tetrahydrofuran Stage #2: ethyl 4-formyl-3-hydroxybenzoate In tetrahydrofuran at -50 - 20℃; for 16h; Stage #3: With water; ammonium chloride In tetrahydrofuran 59.59a (Example 59) 5-Hydroxymethyl-2-(4-methoxymethylbenzyl)phenyl 7-deoxy-D-glycero-β-D-gluco-heptopyranoside (Example Compound No. 1-129); (59a) 5-Acetoxymethyl-2-(4-methoxymethylbenzyl)phenol; 1-Bromo-4-methoxymethylbenzene (2.20 g, 10.9 mmol), metal magnesium (300 mg, 12.3 mmol), a catalytic amount of iodine, and tetrahydrofuran (6.0 mL) were used to prepare Grignard reagent by a usual method. The resulting Grignard reagent was added to a solution of ethyl 4-formyl-3-hydroxybenzoate (532 mg, 2.74 mmol) in tetrahydrofuran (6.0 mL) at -50°C, and the mixture was stirred for 16 h while heated to room temperature. Saturated aqueous ammonium chloride was added to the reaction mixture, the mixture was extracted with ethyl acetate, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (hexane:ethyl acetate, 90:10 to 20:80, v/v) to obtain a crude product (234 mg, yield 27%).
  • 5
  • [ 16881-77-9 ]
  • [ 1122-91-4 ]
  • [ 1515-88-4 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: (dimethoxy)methylsilane; 4-bromo-benzaldehyde With dicarbonyl(pentamethylcyclopentadienyl)(4-methoxyphenyl)iron In dichloromethane for 4h; Inert atmosphere; Irradiation; Schlenk technique; Stage #2: With sodium hydroxide In methanol; water Inert atmosphere; Schlenk technique; General procedure for the reaction of aromatic aldehydes and analytical data General procedure: In a Schlenk tube under 1 atm of argon, a solution of the substrate (2 mmol, 1 equiv), the precatalyst (0.04 mmol, 0.02 equiv), and the silane (3 mmol, 1.5 equiv) in methylene chloride (15 mL) was irradiated for 4h. After removal of the solvent, methanol (5 mL) and aqueous NaOH solution (2.5 M, 5 mL) were added and the resulting suspension was stirred overnight. Neutralization with aqueous HCl solution (2 M, 30 mL) and brine (20 mL) followed by standard workup gave the desired products as pure yellow oils.
  • 6
  • [ 1515-88-4 ]
  • [ 80936-82-9 ]
YieldReaction ConditionsOperation in experiment
85% With ammonium hydroxide; copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 100℃; for 5h; Sealed tube; V.3.2 Synthesis of 4-(methoxymethyl) aniline [5.3b]. 5.3a (1.9 g, 9.45 mmoi, 1.0equiv), CuI (0.180 g, 0.94 mmoi, 0.1 equiv), acetyi acetone (0.95 g, 9.45 mmoi, 1.0 equiv) and C52CO3 (6.15 g, 18.9 mmoi, 2.0 equiv) were suspended in N,N-dimethyiformamide (28mL) in sealed tube and ammonium hydroxide (2.18 mL, 5.67 mmol, 6.0 equiv) was added and the reaction mixture was stirred at 100 °C for 5 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a residue. The residue was purified by silica gel column chromatography (0.7 % MeOH in dichloromethane) to afford product 5.3b (1.1 g, 85 % yield). LCMS (mlz): 138.2 [M+H]. 1H NMR (400 MHz, DMSO) 6 6.96 (d, J = 8.1 Hz, 2H), 6.52 (d, J 8.1 Hz, 2H), 5.06 (s, 2H), 4.18 (s, 2H), 3.19 (s, 3H).
  • 7
  • [ 1515-88-4 ]
  • [ 88-68-6 ]
  • [ 83800-88-8 ]
YieldReaction ConditionsOperation in experiment
81% With oxygen In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Sealed tube; Green chemistry; General procedure for the synthesis of N-heterocyclic compounds General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.
  • 8
  • [ 1515-88-4 ]
  • [ 4141-08-6 ]
  • [ 108237-87-2 ]
YieldReaction ConditionsOperation in experiment
78% With oxygen In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Sealed tube; Green chemistry; General procedure for the synthesis of N-heterocyclic compounds General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.
  • 9
  • [ 1515-88-4 ]
  • [ 137-07-5 ]
  • [ 19654-19-4 ]
YieldReaction ConditionsOperation in experiment
68% With oxygen In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Sealed tube; Green chemistry; General procedure for the synthesis of N-heterocyclic compounds General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.
  • 10
  • [ 1515-88-4 ]
  • [ 73183-34-3 ]
  • [ 675605-92-2 ]
YieldReaction ConditionsOperation in experiment
61% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; Inert atmosphere; 119.A To a solution of 1 -bromo-4-(methoxymethyl)benzene (500 mg, 2.487 mmol) in 1 ,4- dioxane (50 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (947 mg, 3.73 mmol), PdCl2(dppf)-CH2Cl2 adduct (203 mg, 0.249 mmol) and potassium acetate (488 mg, 4.97 mmol). The reaction mixture was heated to 100 °C under N2 and stirred overnight. The mixture was evaporated, water (50 mL) was added, and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated. The residue was purified with silica gel chromatography (ethyl acetate/petroleum ether: 0-1/40) to afford 2-(4- (methoxymethyl)phenyl)-4,4, 5, 5-tetramethyl-1 ,3,2-dioxaborolane (420 mg, 1 .523 mmol, 61 % yield) as a colourless oil.
42 % With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; 8 Preparation 42: 2-(4-(methoxymethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane To a mixture of 1-bromo-4-(methoxymethyl) benzene (3.00 g, 14.9 mmol, 1.00 equiv) and bis(pinacolato)diboron (7.58 g, 29.8 mmol, 2.00 equiv) in 1,4-dioxane (40 mL) was added Pd(dppf)Cl2·CH2Cl2 (1.09 g, 1.49 mmol, 0.100 equiv) and KOAc (2.93 g, 29.8 mmol, 2.00 equiv) at room temperature under a nitrogen atmosphere. The resulting mixture was stirred overnight at 80 °C. The reaction was quenched with water. The resulting mixture was extracted with EtOAc (5 x 50 mL). The combined organic layers were washed with brine (3 x 50 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with EA / MeOH (10:1) to afford the crude product (2.30 g, crude) and further purified by Prep-HPLCO to afford the title compound as a yellow oil (1.56 g, 42%)
  • 11
  • [ 1515-88-4 ]
  • [ 623-00-7 ]
YieldReaction ConditionsOperation in experiment
36% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium acetate; oxygen; nitric acid In acetic acid at 50℃; for 20h; Autoclave; Conversion of Benzyl Ethers into Aryl Nitriles; GeneralProcedure General procedure: The reactions were carried out a ~40 mL, Teflon-lined, stainlesssteelautoclave. AcOH (2 mL), TEMPO (0.25 mmol), HNO3 (0.25mmol), the appropriate benzylic methyl ether (0.5 mmol), andNH4OAc (1.5 mmol) were added sequentially to the autoclave.Subsequently, the autoclave was pressurized to 1 MPa with O2,and the reaction mixture was heated with magnetic stirring at50 °C for 20 h, then cooled to r.t. The mixture was then dilutedwith Et2O (15 mL) and H2O (5 mL), and adjusted to pH 7-8 with2 M aq NaOH. The two layers were separated, and the aqueouslayer was extracted with Et2O (3 × 15 mL). The organic layerswere combined, dried (Na2SO4), filtered, and concentrated to avolume of approximately 3 mL in a rotary evaporator. GC analysisof the concentrated organic phase, with biphenyl or 1,2,4,5-tetramethylbenzene as internal standard, provided the GC yieldof the product. The crude product in the concentrated organicphase from another parallel experiment was purified bycolumn chromatography [silica gel (200-300 mesh), EtOAc-PE].
  • 12
  • [ 121-43-7 ]
  • [ 1515-88-4 ]
  • [ 279262-11-2 ]
YieldReaction ConditionsOperation in experiment
85.7% Stage #1: 1-bromo-4-methoxymethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -80 - -70℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -70 - -30℃; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water Inert atmosphere; 1.1 (1) Synthesis of compound BYLC-01-1 Under the protection of nitrogen, add 40.0g p-bromoanisole, 280ml tetrahydrofuran to the reaction flask, add 0.26mol n-butyllithium n-hexane solution dropwise to the temperature control -70 to -80°C, drip it, and control the temperature for 1 hour;Control the temperature at -60 to -70°C, add 32.0g of trimethyl borate dropwise, and then naturally return to -30°C.400ml of 2M hydrochloric acid aqueous solution was added for acidification, and conventional post-treatment was performed. Petroleum ether was recrystallized to obtain 28.3g of light yellow solid (compound BYLC-01-1), HPLC: 99.7%, yield: 85.7%.
  • 13
  • [ 880652-93-7 ]
  • [ 1515-88-4 ]
  • [ 2647389-95-3 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 1-bromo-4-methoxymethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: 4(7)-bromo-2-methyl-1(3)H-indene With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90℃; 2.2-2 Step 2-2:
Synthesis of 7-(4-methoxymethyl)phenyl)-2-methyl-1H-indene 1-bromo-4-(methoxymethyl)benzene (9.3 g, 46.3 mmol) was dissolved in anhydrous THF (40 under argon (Ar). The temperature was lowered to -78° C., and an n-butyllithium solution (n-BuLi, 2.5 M in hexane, 20.4 mL) was added, followed by stirring at room temperature for 30 minutes. The temperature was lowered again to -78° C., and trimethyl borate (15.5 mL, 139 mmol) was added and then stirred at room temperature overnight. Sat. NH4Cl was added to the reaction solution and then extracted with MTBE. Anhydrous MgSO4 was added and water was removed by filtration. The solution was concentrated under reduced pressure and the subsequent reaction was carried out without further purification. The above obtained compound, 7-bromo-2-methyl-1H-indene (9.63 g, 46.3 mmol), and Na2CO3 (14.7 g, 139 mmol) were added to a mixed solvent of toluene (80 mL), H2O (40 mL), and EtOH (40 mL) and stirred. Pd(PPh3)4 (1.07 g, 2.32 mmol) was added to the above solution and then stirred at 90° C. overnight. After the reaction was completed, MTBE and water were added and the organic layer was separated. Water was removed with anhydrous MgSO4. The obtained solution was concentrated under reduced pressure and then purified by column chromatography (E/H=1/30) to obtain 7-(4-(methoxymethyl)phenyl)-2-methyl-1H-indene (6.9 g, 60%). 1H NMR (500 MHz, CDCl3, 7.24 ppm): 2.15 (3H, s), 3.35 (2H, s), 3.38 (3H, s), 4.48 (2H, s), 6.55 (1H, s), 7.05-7.44 (7H, m)
  • 14
  • [ 1515-88-4 ]
  • [ 214360-73-3 ]
  • [ 2787536-01-8 ]
YieldReaction ConditionsOperation in experiment
96% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; tripotassium phosphate tribasic In 1,4-dioxane; lithium hydroxide monohydrate at 110℃; for 16h; Sealed tube; 138.1 Step 1 : 4'-(methoxymethyl)-[1 ,T-biphenyl]-4-amine: A mixture of 1-bromo-4- (methoxymethyl)benzene (1.0 g, 4.98 mmol), 4-(4,4,5,5-tetramethyl -1 ,3,2-dioxaborolan-2-yl)aniline (1.6 g, 7.46 mmol), K3PO4 (2.1 g, 9.95 mmol) and Pd(dppf)Cl2 (0.36 g, 0.49 mmol) in dioxane/ (v/v=10:1) (20 mL) was heated at 110 °C in a sealed tube for 16 h. The resulting mixture was filtered through celite, concentrated and purified by silica gel chromatography (eluting with 1/5 EtOAc/PE) to afford the title compound (1.02 g, 4.78 mmol, 96% yield) as a yellow solid. 1 H NMR (400 MHz, DMSO-d6) 6 7.56 - 7.49 (m, 2H), 7.41 - 7.28 (m, 4H), 6.69 - 6.61 (m, 2H), 5.35 (s, 2H), 4.41 (s, 2H), 3.30 (s, 3H).
 

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