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Chemical Structure| 89598-96-9 Chemical Structure| 89598-96-9
Chemical Structure| 89598-96-9

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Product Details of 3-Bromophenylboronic acid

CAS No. :89598-96-9
Formula : C6H6BBrO2
M.W : 200.83
SMILES Code : C1=C(C=CC=C1Br)B(O)O
MDL No. :MFCD00239386
InChI Key :AFSSVCNPDKKSRR-UHFFFAOYSA-N
Pubchem ID :2734318

Safety of 3-Bromophenylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Bromophenylboronic 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 [ 89598-96-9 ]

[ 89598-96-9 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 27741-65-7 ]
  • [ 89598-96-9 ]
  • ethyl 2-(1-(3-bromophenyl)cyclobutyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With [Rh(OH)(cod)]2; surfactant TPGS-750-M; potassium carbonate; In water; at 20℃; for 2h;Green chemistry; General procedure: In a 5 mL microwave vial containing alpha,beta-unsaturated ethyl ester (100mg, 1.00equiv), boronic ester (2.00 equiv), potassium carbonate (2.00 equiv) and [RhOH(COD)]2 (0.05 equiv) was added 2% wt. TPGS-750-M solution in water (3 mL). The mixture was stirred vigorously at ambient temperature for the indicated time. The reaction mixture was then extracted with ethyl acetate. The organic phase was subsequently dried over MgSO4, filtrated and reduced under vacuum. The crude product was purified by column chromatography on silica (eluent: 0-10% methanol in dichloromethane) to yield the desired product.
33% With water; potassium hydroxide; In 1,4-dioxane; at 0 - 25℃; for 16h;Inert atmosphere; To a stirred mixture of bis(chlororhodiumcarbaldehyde) (0.35 g, 1.04 mmol) in dioxane (10 mL) was added KOH (7 mL, 2M in water) dropwise at 0-10 C. The mixture was stirred at 0-10 C for 20 min. Then to the mixture was added (3-bromophenyl)boronic acid (5.73 g, 28.53 mmol) and ethyl 2- cyclobutylideneacetate (2.0 g, 14.27 mmol) at 0-10 C. The mixture was stirred at 25 C for 16 h under nitrogen. The mixture was quenched by the addition of water and extracted with EtOAc. The combined organic layer was washed with brine, dried, filtered and concentrated under vacuum. The residue was purified by chromatography to afford the title compound (1.4 g, 33%) as a light-yellow oil.
  • 3
  • [ 40000-20-2 ]
  • [ 89598-96-9 ]
  • 5-(3-bromophenyl)[1,10]phenanthroline [ No CAS ]
YieldReaction ConditionsOperation in experiment
After the intermediate product (D) 10.0 g (34.56 mmol)of the equation 2 and 2 - (3-Bromo-phenyl) -4,6-diphenyl - [1,3,5] triazine (2-Bromo-4,6-diphenyl - [1,3,5] triazine and 4'-1-Bromo-3-Phenyl boronicacid are synthesized to the Suzuki coupling.) 14.76 g (38.02 mmol), the NaO (t-Bu) 4.98 g (51.84 mmol), and the Pd 2 (dba)3 0.94 g (1.04mmmol) were suspended in the toluene 140 mL P (t-Bu) 3 0.50 mL (2.07 mmol) was put and it mixed reflux under the nitrogen air current for 24 hours. It extracts in the dichloromethane and distilled water and the organic layer the silica gel is filtered. Hexane theorganic solution is removed: it recrystallized as the dichloromethane and ethyl acetate and the compound I-51 14.44g (yield : 70 percent) was obtained by the dichloromethane = 7 : 3 (v/v) after the silica gel column.
  • 4
  • [ 955368-90-8 ]
  • [ 89598-96-9 ]
  • [ 1147706-69-1 ]
YieldReaction ConditionsOperation in experiment
69% With pyridine; copper diacetate; In chloroform; at 20℃; for 120h; Pyridine (1.46 mL, 18.0 mmol) was added to a stirred solution of 2-allyl-6- (methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (500 mg, 2.25 mmol) [Prepared according to EP2213673B1 (Production Example 1, p37)], copper(ll) acetate (409 mg, 2.25 mmol) and (3-bromophenyl)boronic acid (745 mg, 3.71 mmol) in chloroform (5.0 mL) at RT in an open flask. After 5 days, ammonium hydroxide solution (aq) (30 mL) and brine (30 mL) were added and the resulting mixture was extracted using EtOAc (3 x 20 mL). The combined organic phase was dried (Phase Separator), the solvents were removed in vacuo and the remaining residue was purified by flash chromatography (0-100%, EtOAc in cyclohexane) to give the title compound (587 mg, 69%) as an orange solid.LCMS (Method A): RT = 1.38 mi mlz = 377, 379 [M+H]
  • 5
  • [ 955368-90-8 ]
  • [ 89598-96-9 ]
  • 1-(3-[dimethyl(oxo)-λ6-sulfanylidene]amino}phenyl)-6-(methylsulfanyl)-2-(prop-2-en-1-yl)-1H,2H,3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]
  • 6
  • [ 54151-74-5 ]
  • [ 89598-96-9 ]
  • (2-(3-bromophenyl)-4-phenylpyridine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 12h;Reflux; 3 grams (g) (13 millimoles, mmol) of 2-bromo-4- phenylpyridine, 3.1 g (1.2 equivalents, equiv.) of (3-bro- mophenyl)boronic acid, 1.1 g (0.9 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.4 g (32 mmol, 3 equiv.) of sodium carbonate were mixed with 49 milliliters (mE) of a solvent in which tetrahydrofuran (THF) and distilled water (H20) were mixed at a volume ratio of 3:1, and then refluxed for 12 hours. A reaction product obtained therefrom was cooled to room temperature, and a precipitate was filtered therefrom to obtain a filtrate. Then, the filtrate was washed by using ethyl acetate (EA)/H20, and purified by column chromatography (while increasing a rate of MC (methylene chloride)/Hex (hexane) to between 25% and 50%) to obtain 3.2 g (yield: 80%) of Intermediate A. The obtained compound was identified by mass spectrometry and HPEC analysis. HRMS (MALDI) calcd for C17H12BrN: mlz 309.0153, Found: 309.0155.
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 12h;Reflux; 3 grams (g) (13 millimoles, mmol) of <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong>, 3.1 g (1.2 equivalents, equiv.) of (3-bromophenyl)boronic acid, 1.1 g (0.9 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.4 g (32 mmol, 3 equiv.) of sodium carbonate were mixed with 49 milliliters (mL) (0.6 molar, M) of a solvent in which tetrahydrofuran (THF) and distilled water (H2O) were mixed at a volume ratio of 3:1, The reaction mixture was then refluxed for 12 hours. The reaction product obtained therefrom was cooled to room temperature, and the precipitate was filtered to obtain a filtrate. The filtrate was washed with ethyl acetate (EA)/H2O, and the crude product was purified by column chromatography (while increasing a rate of MC(methylene chloride)/Hex(hexane) to between 25% and 50%) to obtain 3.2 g (yield: 80%) of Intermediate A. The obtained compound was identified by mass spectroscopy and HPLC analysis. (0411) HRMS (MALDI) calcd for C17H12BrN: m/z 309.0153, Found: 309.0155.
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 12h;Reflux; 3 grams (g) (13 millimoles (mmol)) of <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong>, 3.1 g (1.2 equivalents (equiv.)) of (3-bromophenyl)boronic acid, 1.1 g (0.9 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.4 g (32 mmol, 3 equiv.) of sodium carbonate were mixed with 49 milliliters (mL) of a solvent (0.6 molar (M)) in which tetrahydrofuran (THF) and distilled water (H2O) were mixed at a ratio of 3:1, and then refluxed for 12 hours. The resultant mixture was cooled to room temperature, and a precipitate was filtered. The filtrate obtained therefrom was washed by using ethyl acetate (EA) and H2O and purified by column chromatography (while increasing a rate of MC/Hex to between 25% to 50%) to obtain 3.2 g (yield: 80%) of Intermediate A. The obtained product was identified by Mass and HPLC analysis. HRMS (MALDI) calcd for C17H12BrN: m/z 309.0153, Found: 309.0155.
 

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