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Chemical Structure| 5720-06-9 Chemical Structure| 5720-06-9
Chemical Structure| 5720-06-9

2-Methoxyphenylboronic acid

CAS No.: 5720-06-9

4.5 *For Research Use Only !

Cat. No.: A109135 Purity: 98%

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Product Details of 2-Methoxyphenylboronic acid

CAS No. :5720-06-9
Formula : C7H9BO3
M.W : 151.96
SMILES Code : OB(C1=CC=CC=C1OC)O
MDL No. :MFCD00236047
InChI Key :ROEQGIFOWRQYHD-UHFFFAOYSA-N
Pubchem ID :2733958

Safety of 2-Methoxyphenylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of 2-Methoxyphenylboronic acid

* 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 [ 5720-06-9 ]

[ 5720-06-9 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 5720-06-9 ]
  • [ 342777-09-7 ]
  • [ 939-57-1 ]
  • (E)-3-[2-(2-Methoxy-benzyl)-phenyl]-acrylic acid [ No CAS ]
  • 2
  • [ 5720-06-9 ]
  • [ 1122-91-4 ]
  • [ 421553-62-0 ]
YieldReaction ConditionsOperation in experiment
87% With sodium carbonate; In methanol; at 20.0℃; for 3.0h;Sealed tube; Inert atmosphere; General procedure: To a round bottom flask with stir bar were added phenylboronic acid (275 mmol), 1-bromo-4-nitrobenzene (250 mmol), base (375 mmol), 1.0 mol% catalyst 6 (9.2 mg), and solvent 4mL. The entrance was sealed with septum, and inside air was was exchanged with N2. After the mixture was stirred at room temperature for a certain period, the mixture was diluted with H2O (5ml) and Et2O (5 ml). Organic layer was concentrated in vacuo.
81% With sodium carbonate; at 90.0℃; for 1.0h; General procedure: Suzuki-Miyaura coupling was carriedout in a batch reactor using Pd-RGO synthesized with amicroreactor. Aryl bromide (250 mumol), arylboronic acid(275 mumol), and Na2CO3 (0.38 mmol) together with the Pd-RGO synthesized above are added to a 5 mL round bottomflask and stirred at 90C for 1 h. After the reaction, the mixtureextracted with dichloromethane (3 × 5 mL) and impuritieswere removed using celite. MgSO4 was used to removethe remaining H2O, product was obtained from extractedDCM solution through rotary evaporator. We purified theextracted product by the thin-layer chromatography and liquidcolumn chromatography using hexane and ethyl acetate(9: 1). The analysis was carried out via 1H and 13C NMR.
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; water; toluene;Reflux; General procedure: Tetrakis(triphenylphosphine)palladium(0) (0.0168 mmol) was added to a solution of 4-bromobenzaldehyde (50, 5.6 mmol) in ethanol-toluene (40 mL, 1:1). After 15 min, the appropriate boronic acid 51b-m (6.75 mmol) was added, followed by sodium hydrogen carbonate (22.4 mmol) and water (11 mL). The resulting mixture was heated under reflux for 9-15 hours. After cooling, the reaction mixture was filtered through Celite, the organic phase was separated, washed with brine (2x20 mL), dried and the solvent evaporated in vacuo. The residue thus obtained was purified by flash-chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds.
  • 3
  • [ 29022-11-5 ]
  • [ 5720-06-9 ]
  • [ 210282-31-8 ]
  • 2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • [(5S,10bR)-8-(2-Methoxy-phenyl)-3-oxo-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline-5-carbonyl]-amino}-acetic acid [ No CAS ]
  • 4
  • [ 29022-11-5 ]
  • [ 5720-06-9 ]
  • [ 210282-31-8 ]
  • 2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 2-{2-[1-(carboxymethyl-carbamoyl)-2-(2'-methoxy-biphenyl-3-yl)-ethylcarbamoyl]-ethyl}-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 5
  • [ 29976-20-3 ]
  • [ 5720-06-9 ]
  • C21H21NO2 [ No CAS ]
  • 7
  • potassium phosphate [ No CAS ]
  • [ 2142-68-9 ]
  • [ 5720-06-9 ]
  • [ 224311-51-7 ]
  • 2-methoxy-2'-acetylbiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
201 mg (89%) palladium diacetate; In toluene; EXAMPLE 42 Synthesis of 2-methoxy-2'-acetylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and toluene (3 mL) and 2'-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 65° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 201 mg (89percent) of the title compound.
201 mg (89%) palladium diacetate; In toluene; Example 42 Synthesis of 2-methoxy-2'-acetylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and toluene (3 mL) and 2'-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 65° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 201 mg (89percent) of the title compound.
  • 8
  • [ 106-43-4 ]
  • [ 5720-06-9 ]
  • [ 224311-51-7 ]
  • [ 92495-53-9 ]
YieldReaction ConditionsOperation in experiment
188 mg (95%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 41 Synthesis of 2-methoxy-4'-methylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 4-chlorotoluene (0.144 ml, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 188 mg (95percent) of the title compound.
188 mg (95%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 41 Synthesis of 2-methoxy-4'-methylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 4-chlorotoluene (0.144 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 188 mg (95percent) of the title compound.
  • 9
  • [ 1532-71-4 ]
  • [ 5720-06-9 ]
  • [ 134948-96-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 50℃; for 12h; Stage A: 1 -(2-methoxyphenyl)isoquinoline.A solution of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> (2.06 g, 10 mmol), prepared as described in EuropeanJournal of Organic Chemistry 2002, 4181-4184, 2-methoxyphenylboronic acid (2.79 g, 10 mmol), Pd(PPh3)4 (5percentmol), K2CO3 (5g) in DMF/water (3/1) is stirred at 500C for 12 hours.The reaction mixture is then pored on water (150 mL). The aqueous phase is extracted with EPO <DP n="84"/>ethyl acetate (3xl00mL). The combined organic layers are washed with water (3x200mL).The organic phase is dried over magnesium sulfate and evaporated under vacuum to afford the title compound.
  • 10
  • [ 623-12-1 ]
  • [ 5720-06-9 ]
  • [ 182482-25-3 ]
  • [ 1206164-33-1 ]
  • [ 49602-47-3 ]
  • 11
  • [ 5720-06-9 ]
  • p-halobenzaldehyde [ No CAS ]
  • [ 421553-62-0 ]
  • 13
  • [ 890315-72-7 ]
  • [ 5720-06-9 ]
  • [ 1237518-13-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; for 2.5h;Reflux; Inert atmosphere; Reference Example 35a; Water (9.0 mL), sodium carbonate (2.6 g), 2-methoxyphenylboronic acid (1.8 g), and bis(triphenylphosphine)palladium(II) dichloride (0.14 g) were added to an ethylene glycol dimethyl ether (30 mL) solution of <strong>[890315-72-7]tert-butyl 4-bromo-2-nitrobenzoate</strong> (3.0 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate] to obtain 3.3 g of tert-butyl 4-(2-methoxyphenyl)-2-nitrobenzoate as a light yellow oily substance.1H-NMR (CDCl3) delta: 1.58 (9H, s), 3.83 (3H, s), 6.99-7.04 (1H, m), 7.04-7.10 (1H, m), 7.32 (1H, dd, J=7.6, 1.7 Hz), 7.40 (1H, ddd, J=8.3, 7.6, 1.7 Hz), 7.73-7.77 (1H, m), 7.78 (1H, dd, J=7.9, 1.6 Hz), 8.01 (1H, d, J=1.0 Hz).
  • 14
  • potassium phosphate [ No CAS ]
  • [ 1221398-11-3 ]
  • [ 5720-06-9 ]
  • [ 603-35-0 ]
  • 2-chlorobenzofuro[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
palladium diacetate; In water; acetonitrile; Potassium phosphate (12.72 g, 60 mmol), triphenyl phosphine (0.682 g, 2.40 mmol), <strong>[1221398-11-3]6-chloro-5-iodo-2-aminopyridine</strong> (6.1 g, 24 mmol), 2-methoxybenzeneboronic acid (5.10 g, 33.5 mmol) and palladium acetate (0.27 g, 1.20 mmol) were sequentially added to degassed acetonitrile (200 mL) and water (60 mL) under nitrogen. The reaction mixture was heated at 75 C. for overnight, then cooled to room temperature. The organic layer was separated and aqueous layer and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified by silica column using hexanes and ethyl acetate as eluent furnishing 4.05 g of title compound. Synthesis of 2-chlorobenzofuro[2,3-b]pyridine:
  • 15
  • [ 109179-31-9 ]
  • [ 5720-06-9 ]
  • [ 94235-91-3 ]
  • 16
  • [ 3141-24-0 ]
  • [ 5720-06-9 ]
  • [ 1415482-25-5 ]
  • 17
  • [ 10323-39-4 ]
  • [ 5720-06-9 ]
  • [ 1609538-17-1 ]
  • 18
  • [ 5720-06-9 ]
  • [ 873-76-7 ]
  • [ 421553-62-0 ]
  • 19
  • [ 5720-06-9 ]
  • [ 56844-40-7 ]
  • 6-(2-methoxyphenyl)thieno[2,3-d]pyrimidin-4 (3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 110℃; for 5.0h;Inert atmosphere; Compound 5 (1.00 g, 4.33 mmol) was mixed with (2-methoxyphenyl)boronic acid (795 mg, 5.23 mmol), fine powdered K2CO3 (1.44 g, 10.39 mmol), Pd(PPh3)4 (50 mg, 0.04 mmol) and 1/1 1,4-dioxane/water (30 mL). The reaction was then stirred at 110 C for 5 h under nitrogen atmosphere. The solvent was removed and the product was diluted with water (50 mL). The mixture was filtered and the solid material washed with water (2×75 mL). This was used without further purification. Drying gave 1.02 g (3.95 mmol, 91%) of 6 as a light brown solid, mp 317 C (dec.); 1H NMR (400 MHz, DMSO-d6) delta: 12.48 (s br, 1H), 8.12 (s, 1H), 7.85-7.81 (m, 2H), 7.41-7.35 (m, 1H), 7.21-7.16 (m, 1H), 7.08-7.03 (m, 1H), 3.95 (s, 3H); 13C NMR (100 MHz, DMSO-d6) delta: 163.8, 157.2, 155.3, 146.3, 135.3, 129.8, 128.0, 124.6, 121.2, 120.3, 118.6, 112.4, 55.8; IR (neat, cm-1): 3070, 1668, 1456, 1265, 1020, 865, 775, 759; HRMS (APCI/ASAP, m/z): 259.0537 (calcd. C13H11N2O2S, 259.0541, [M+H]+).
264 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 110℃; for 5.0h;Inert atmosphere; Under an argon atmosphere, 400 mg of 6-bromothieno [2,3-d] pyrimidin-4 (3H)316 mg of 2-methoxyphenylboronic acid, 200 mg of tetrakis (triphenylphosphine) palladium, and 526 mg of anhydrous potassium carbonate was added a 1,4-dioxane-water 1: 1 mixed solvent (9.6 mL), and the mixture was stirred at 110 C. for 5 hours. The temperature was returned to room temperature, the solvent was distilled off under reduced pressure, neutralized with saturated aqueous ammonium chloride solution, and extracted 8 times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered through a filter paper, and the solvent was distilled off under reduced pressure. The resulting solid was decanted with methanol four times, washed and dried under reduced pressure to give 264 mg of the title compound as a pale yellow solid.
  • 20
  • [ 5720-06-9 ]
  • [ 15164-44-0 ]
  • [ 421553-62-0 ]
  • 21
  • [ 16932-45-9 ]
  • [ 5720-06-9 ]
  • [ 70388-58-8 ]
  • 23
  • [ 5720-06-9 ]
  • [ 366496-33-5 ]
  • 3-fluoro-5-methoxy-2-(2-methoxyphenyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 48.0h; General procedure: To a re-sealable pressure tube (13 x 100 mm) equipped with magnetic stir bar were added o-bromonitrobenzene 1 (0.25 mmol, 100 mol%), aryl boronic acid 2 (0.65 mmol, 260 mol%), Pd(OAc)2 (0.0125 mmol, 5 mol%), PPh3 (1.25 mmol, 500 mol %), K2CO3 (1 mmol, 400 mol%) and o-DCB (1.25 mL, 0.2 M concentration with respect to o-bromonitrobenzene 1. The mixture was heated at 180 C (oil bath temperature) for 48 h, at which point the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was filtered through a pad of celite and the resulting liquor was concentrated in vacuo and purified by flash column chromatography (SiO2) under the conditions noted to furnish the corresponding product.
  • 24
  • [ 7089-68-1 ]
  • [ 5720-06-9 ]
  • [ 145578-47-8 ]
  • 25
  • [ 5720-06-9 ]
  • [ 118289-17-1 ]
  • 2-(2-methoxyphenyl)isonicotinaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.6% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 92℃; for 3h;Inert atmosphere; 2-Bromopyridine-4-carbaldehyde (376 mg, 2.021 mmol), toluene (7 mL), K2C03 aqueous solution (2.76 g potassium carbonate dissolved in 10 mL of water, 2 mL), tetrakis(triphenylphosphine) in a 50 mL two-necked flask Palladium (45,2 mg, 0.04 mmol) was stirred under nitrogen at room temperature for 15 minutes, then 2-methoxyphenylboronic acid (407.6 mg, 2.682 mmol) in absolute ethanol (3 mL) was added and the reaction was heated at 92C. After 3 hours, the reaction system was poured into water and extracted with ethyl acetate. The ethyl acetate layers were combined, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, suction-filtered, the filtrate was concentrated under reduced pressure, concentrate was separated and purified by column chromatography (petroleum ether: ethyl acetate = 6: 1) to give a white solid 406.2mg, yield 73.6%
73.6% General procedure: To a 50 mL two-necked flask equipped with magnetic stirrer and condenser was added 2-bromopyridine (1.0 eq), Pd(PPh3)4 (5 mol%), K2CO3 solution (2.0 eq) and toluene under N2 at room temperture. After reacted for 15 min, a solution of the boronic acid (1.2 eq) in EtOH was then added. The reaction mixture was then heated to 95 C and reacted for 4 h. After cooling to room temperature, to the reaction mixture aqueous NH4Cl was added and extracted three times with EtOAc. The organic extracts were then combined, washed with brine, dried with MgSO4 and then concentrated under reduced pressure. The crude product was then purified by silica gel column chromatography(Petroleum ether/EtOAc) to give compounds 1 and 5
  • 26
  • [ 953039-63-9 ]
  • [ 5720-06-9 ]
  • C15H10ClFN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 120℃; for 16.0h;Inert atmosphere; Compound 21-c (1.03 g, 3.93 mmol), o-methoxyphenylboronic acid (600 mg, 3.95 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (150 mg, 0.2 mmol) and sodium carbonate (1.2 g, 11.3 mmol) were dissolvedin 1,4-dioxane (30 mL) and water (10 mL). The reaction mixture was replaced with nitrogen three times to remove theoxygen inside the system and then heated at 120C for 16 hours. The reaction mixture was cooled to room temperature,diluted with ice water (10 mL) and extracted with dichloromethane (50 mL 3 3). The combined organic phases werewashed successively with water (20 mL 3 3) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and thefiltrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleumether: ethyl acetate = 5: 1) to deliver a white solid 21-b (0.49 g, yield: 43%). LC-MS (ESI): m/z = 599 [M+H]+.
0.49 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 120℃; for 16.0h;Inert atmosphere; Compound 46-c (1.03 g, 3.93 mmol), o-methoxyphenylboronic acid (600 mg, 3.95 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (150 mg, 0.2 mmol) and sodium carbonate (1.2 g, 11.3 mmol) were dissolved in 1,4-dioxane (30 mL) and water (10 mL). The reaction solution was purged with nitrogen gas for three times to remove the oxygen contained in the system, and then heated at 120 C. for 16 hours. The reaction was cooled to room temperature, diluted with ice water (10 mL) and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with water (20 mL×3) and brine (20 mL) sequentially, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate=5:1) to give 46-b as a white solid (0.49 g, yield 43%). LC-MS (ESI): m/z=599[M+H]+.
  • 27
  • [ 5720-06-9 ]
  • [ 5350-41-4 ]
  • [ 883-90-9 ]
  • 28
  • [ 172921-33-4 ]
  • [ 5720-06-9 ]
  • 4-chloro-2,5-difluoro-2’-methoxy-1,1’-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 30.0h;Reflux; Inert atmosphere; Under nitrogen, <strong>[172921-33-4]1-bromo-4-chloro-2,5-difluorobenzene</strong> (12 g, 52.8 mmol),(2-methoxyphenyl) boronic acid (8.42 g, 55.4 mmol), and potassium carbonate (14.58 g, 106 mmol)Is dissolved in a mixture of toluene (100 ml) / water (20 ml),A colorless suspension was obtained. Tetrakis (triphenylphosphine) palladium (0) (0.544 g, 0.528 mmol)Was added to the reaction mixture all at once. Degas the reaction mixture,Heated to reflux under nitrogen for 16 hours.According to the results of gas chromatograph mass spectrometry (GCMS) analysis, the reaction was not completed. Therefore,> 7 g boronic acid as catalyst, 1 g K2CO3,And 0.6 g of Pd (PPh3) 4,The resulting mixture was degassed and refluxed for 14 hours under nitrogen.The reaction mixture is then cooled, the organic phase is separated off and evaporated,Purify by silica gel column chromatography eluting with heptane as a yellow oil,4-Chloro-2,5-difluoro-2'-methoxy-1,1'-biphenyl was obtained.(11.0 g, 82% yield).
82% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 30.0h;Inert atmosphere; Reflux; <strong>[172921-33-4]1-Bromo-4-chloro-2,5-difluorobenzene</strong> (12 g, 52.8 mmol), (2-methoxyphenyl)boronic acid (8.42 g, 55.4 mmol), and potassium carbonate (14.58 g, 106 mmol) were dissolved in a toluene (100 ml)/ water (20 ml) mixture under nitrogen to give a colorless suspension. Tetrakis(triphenylphosphine)palladium(0) (0.544 g, 0.528 mmol) was added to the reaction mixture in one portion. The reaction mixture was degassed and heated to reflux under nitrogen for 16 h. Based on the results of gas chromatography-mass spectroscopy (GCMS) analysis the reaction was not complete. Thus, 7 g more boronic acid, 1 g of K2CO3, and 0.6 g of Pd(PPh3)4 as catalyst was added, and the resulting mixture was degassed and refluxed under nitrogen for 14 h. The reaction mixture was then cooled down and the organic phase was separated, evaporated, and purified by column chromatography on silica gel, eluted with heptanes to yield 4-chloro-2,5-difluoro-2?-methoxy-1,1?-biphenyl (11.0 g, 82% yield) as yellow oil.
  • 29
  • [ 5720-06-9 ]
  • [ 39549-79-6 ]
  • 2-(2-methoxyphenyl)-7-methyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one [ No CAS ]
 

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