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Chemistry
Organometallic Reagents
Organoboron
Methyl 3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
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[ CAS No. 1004294-79-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1004294-79-4
Chemical Structure| 1004294-79-4
Structure of 1004294-79-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1004294-79-4 ]

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SDS Specification
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Product Details of [ 1004294-79-4 ]

CAS No. :1004294-79-4 MDL No. :MFCD12546597
Formula : C14H19BO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 278.11 Pubchem ID :-
Synonyms :

Safety of [ 1004294-79-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1004294-79-4 ]

* 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 [ 1004294-79-4 ]

[ 1004294-79-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 192810-12-1 ]
  • [ 73183-34-3 ]
  • [ 1004294-79-4 ]
YieldReaction ConditionsOperation in experiment
96% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 2 methyl 3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Methyl 3-bromo-5-hydroxybenzoate (26 g, 112.5 mmol), bis(pinacolato)diborane(31.4 g, 123.8 mmol) and potassium acetate (33.1 g, 337.6 mmol) were dissolved in1,4-dioxane (450 mL) and the solution degassed with a stream of nitrogen for 10 mi Pd(dppf)C12.CH2CI2 (4.6 g, 5.62 mmol) was added and the resulting solution degassed with a stream of nitrogen for a further 5 mm before the reaction mixture was stirred at 100 °C for 16 h. The reaction mixture was filtered through Celiteand concentrated in vacuo to give a brown solid. The crude material was purified by dry flash silica chromatography (eluting with 0 - 25% EtOAc in heptanes). Product containing fractions were concentrated, the material slurried in heptane and the solid collected by filtration to give the title compound 30.1 g (96 % yield) as a cream powder.
83% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere; 16 Methyl 3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Methyl 3-hydroxy-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate Methyl 3-bromo-5-hydroxybenzoate (1 g, 4.33 mmol) was dissolved in 40 mL dioxane. Bis(pinacolato)diboron (2.2 g, 8.66 mmol) and potassium acetate (1 .27 g, 12.94 mmol) were added and the mixture was submitted to three vacuum-argon cycles. Bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.18 g, 0.22 mmol) was added under argon conditions. The mixture was heated at 90°C overnight. The mixture was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1Purification System (0% to 10%, dichloromethane-methanol) to obtain 1 g (83% yield) of the title compound as a brown solid. Purity 100%.LRMS (m/z): 279 (M+1 )+.
Reference： [1]Current Patent Assignee: EVOTEC AG; BAYER AG - WO2016/91776, 2016, A1 Location in patent: Page/Page column 140; 141
[2]Current Patent Assignee: ALMIRALL SA - WO2014/60432, 2014, A1 Location in patent: Page/Page column 130; 131
  • 2
  • [ 41731-23-1 ]
  • [ 1004294-79-4 ]
  • methyl 3-hydroxy-5-(5-methyl-1,3-thiazol-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; water; at 90℃; for 17h;Inert atmosphere; Intermediate 2 (1.0 g, 3.60 mmo[) and 2-bromo-5-methy[-1,3-thiazo[e (0.451 mL, 4.32 mmo[) were dissolved in 1M K2C03 aqueous solution (8.63 mL) and THF (58.7 mL). The solution was degassed with a stream of nitrogen for 10 minutes, [1,1- Bis(diphenylphosphino)ferrocene] palladium(II) dichloride (395.3 mg, 0.539 mmol)was added and the reaction mixture heated at 90 C for 17 h until reaction completion (monitored by TLC). The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organics were dried (over MgSO4) and concentrated under reduced pressure. Crude material was purified by Biotage IsoleraTM chromatography (eluting with 12 - 80 % EtOAc inheptane on a 25 g pre-packed KP-Si02 column) to give 359.7 mg (40% yield) of the title compound as an off-white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 8.06 (t, J = 1.4 Hz, 1H), 7.67 - 7.62 (m,1H), 7.54 (dd, J = 2.5, 1.4 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H), 5.84 (5, 2H), 3.93 (5,3H), 2.53 (d, J = 1.1 Hz, 3H).
Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 141
  • 3
  • [ 857549-84-9 ]
  • [ 1004294-79-4 ]
  • methyl 3-(5-ethyl-1,3-thiazol-2-yl)-5-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran Reflux; 3A methyl 3-(5-ethyl-1,3-thiazol-2-yl)-5-hydroxybenzoate A mixture of Intermediate 2 (7.08 g, 25.5 mmol), 2-chloro-5-ethyl-1,3-thiazole (4.51 g, 30.5 mmol), [1,1, -Bis-(diphenylphosphino)-ferrocen] -palladium(II)dichloride (3.12 g, 3.82 mmol), and K2C03 (31 ml, 2.0 M, 61 mmol) in THF (420 mL)was stirred at ref[ux unti[ comp[ete conversion. The so[vent was evaporated under reduced pressure, water added and the mixture extracted with EtOAc. The combined organic [ayers were washed with saturated aqueous NaC[-so[ution and evaporated to dryness under reduced pressure. Crude materia[ was purified byco[umn chromatography (si[ica ge[, hexane / EtOAc gradient) to give 2.54 g (38% yie[d) of the tit[e compound.1H NMR (400 MHz, DMSO-d6): ö [ppm] 1.26 - 1.32 (m, 3 H) 2.89 (m, 2 H) 3.87 (5, 3 H) 7.39 (dd, 1 H) 7.52 (dd, 1 H) 7.66 (t, 1 H) 7.87 (t, 1 H) 10.24 (5, 1 H).
Reference： [1]Current Patent Assignee: BAYER AG; EVOTEC AG - WO2016/91776, 2016, A1 Location in patent: Page/Page column 141; 142
  • 4
  • [ 1004294-79-4 ]
  • [ 16629-15-5 ]
  • methyl 3-(5-chloro-1,3-thiazol-2-yl)-5-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran;Reflux; A mixture of Intermediate 2 (30.1 g, 50% purity, 54.2 mmo[), 2-bromo-5-ch[oro-1 ,3-thiazo[e (14.0 g, 70.4 mmo[), [1,1, -Bis-(dipheny[phosphino)-ferrocen]pa[[adium(II) dich[oride (6.63 g, 8.13 mmo[), and K2C03 (65 mL, 2.OM, 130 mmo[)in THF (890 mL) was stirred at ref[ux unti[ comp[ete conversion. The so[vent was evaporated under reduced pressure, water added and the mixture extracted with EtOAc. The combined organic [ayers were washed with saturated aqueous NaC[so[ution and evaporated to dryness under reduced pressure. Crude materia[ was purified by co[umn chromatography (si[ica ge[, hexane / EtOAc gradient) to give5.21 g (34% yie[d) of the tit[e compound.1H NMR (400 MHz, DMSO-d6): oe [ppm] 3.85 - 3.90 (m, 3 H) 7.44 (dd, 1 H) 7.51 (dd, 1 H) 7.84 (t, 1 H) 7.99 (5, 1 H) 10.35 (br. s., 1 H).
Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 142

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