[ CAS No. 515131-35-8 ]

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2D
Chemical Structure| 515131-35-8
Chemical Structure| 515131-35-8
Structure of 515131-35-8

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Product Details of [ 515131-35-8 ]

CAS No. :515131-35-8MDL No. :MFCD09261433
Formula :C14H19BO4Boiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :262.11Pubchem ID :16086086
Synonyms :

Computed Properties of [ 515131-35-8 ]

TPSA : 55.8 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.50 Rotatable Bond Count : 2

Safety of [ 515131-35-8 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 515131-35-8 ]

  • Upstream synthesis route of [ 515131-35-8 ]
  • Downstream synthetic route of [ 515131-35-8 ]

[ 515131-35-8 ] Synthesis Path-Upstream   1~2

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  • [ 73183-34-3 ]
  • [ 515131-35-8 ]
YieldReaction ConditionsOperation in experiment
71% With potassium acetate In N,N-dimethyl-formamide at 100℃; for 6.00 h; Inert atmosphere Reference Example 8
4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) benzoic acid (Compound A8)
3-Iodo-4-methyl benzoic acid (26.2 g, 100 mmol) was dissolved in DMF (300 mL), and then bis(pinacolate)diboron (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium (8.17 g, 10.0 mmol) and potassium acetate (49.0 g, 500 mmol) were added thereto, followed by stirring under argon atmosphere at 100°C for 6 hours.
To the reaction mixture was added 1 mol/L of hydrochloric acid, followed by extraction with ethyl acetate, an organic layer was washed with brine, followed by drying over anhydrous magnesium sulfate, and activated carbon (1 g) was added thereto, followed by stirring at room temperature for 1 hour.
The reaction mixture was filtered through celite, followed by washing with ethyl acetate:
The solvent was evaporated, and the resulting crystals were recrystallized from isopropyl ether, followed by filtration to obtain Compound A8 (18.5 g, 71percent).
1H NMR (300 MHz, CDCl3) δ (ppm) 1.36 (s, 12H), 2.61 (s, 3H), 7.26 (d, J = 8.1 Hz, 1H), 8.02 (dd, J = 8.1, 1.8 Hz, 1H), 8.49 (d, J = 1.8 Hz, 1H).
65% With potassium acetate In N,N-dimethyl-formamide at 80℃; REFERENCE EXAMPLE 19; 4-Methyl-3-(4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)benzoic acid; To a solution of 3-iodo-4-methylbenzoic acid (3.71 g, 14.2 mmol) in DMF (130 mL), bis(pinacolato)diboron (7.20 g, 28.4 mmol), [1 ,1'-bis(diphenylphosphino) EPO ferrocene]dichloro-palladium (II) (1.04 g, 1.28 mmol) and potassium acetate (6.95 g, 70.9 mmol) were added under argon. The mixture was heated at 80 0C overnight and then allowed to cool to room temperature. The solvent was evaporated and the residue was diluted with water and EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed twice with 3N HCI and dried over Na2SO4. The solvent was evaporated and the crude product thus obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford the title compound impurified with starting bis(pinacolato)diboron. The product was slurried in hexane, filtered and dried under vacuum to afford 2.41 g of pure material (yield: 65percent). 1H NMR (300 MHz1 CDCI3) δ (TMS): 1.36 (s, 12 H), 2.61 (s, 3 H)1 7.25 (d, J = 8.1 Hz1 1 H), 8.02 (dd, J = 8.1 Hz1 J1 = 2.1 Hz, 1 H)1 8.48 (d, J = 2.1 Hz, 1 H). LC-MS (method 1): tR = 7.57 min; m/z = 261.0 [M-H]".
Reference: [1] Patent: EP2269993, 2011, A1. Location in patent: Page/Page column 53
[2] Patent: WO2007/339, 2007, A1. Location in patent: Page/Page column 44-45
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 19, p. 5671 - 5686
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4428 - 4432
[5] Patent: WO2006/104917, 2006, A2. Location in patent: Page/Page column 78-79
[6] Patent: WO2003/93248, 2003, A1. Location in patent: Page/Page column 27-28
[7] Patent: US2007/54916, 2007, A1. Location in patent: Page/Page column 29
[8] Patent: WO2004/10995, 2004, A1. Location in patent: Page/Page column 27
[9] Patent: WO2006/104915, 2006, A2. Location in patent: Page/Page column 123
[10] Patent: WO2006/104889, 2006, A2. Location in patent: Page/Page column 115-116
[11] Patent: WO2007/147104, 2007, A2. Location in patent: Page/Page column 76
[12] Patent: WO2007/147103, 2007, A2. Location in patent: Page/Page column 108-109
[13] Patent: WO2007/147109, 2007, A2. Location in patent: Page/Page column 103-104
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3909 - 3913[2] Angew. Chem., 2016, p. 3977 - 3981,5
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