B-(4-Ethoxy-2,3-difluorophenyl)boronic acid
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B-(4-Ethoxy-2,3-difluorophenyl)boronic acid
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CAS No:
212386-71-5
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Formula:
C8H9BF2O3
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Chemical Name:
B-(4-Ethoxy-2,3-difluorophenyl)boronic acid
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Synonyms:
Boronic acid,B-(4-ethoxy-2,3-difluorophenyl)-;Boronic acid,(4-ethoxy-2,3-difluorophenyl)-;B-(4-Ethoxy-2,3-difluorophenyl)boronic acid;4-Ethoxy-2,3-difluorophenylboronic acid;(2,3-Difluoro-4-ethoxyphenyl)boronic acid
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CAS No:
Characteristics
49.7
0.04330
1.29
135-136 °C @ Solvent: Toluene
316°C at 760 mmHg
144.9±30.7 °C
1.484
0mmHg at 25°C
Safety Information
Xi
|Warning|H302 (66.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
B-(4-Ethoxy-2,3-difluorophenyl)boronic acid Use and Manufacturing
250 mL three flask was added 15.8g (0.1mol) 2, 3-difluorophenyl ether, tetrahydrofuran, 100ml, with nitrogen replacement air, cooled to -60 ° C, wasadded dropwise 2.5M n-butyllithium 44ml (0.11mol), After the addition stirring.The reaction for half an hour, a solution of trimethyl borate 11.5g (0.11mol), plus after any of its natural warming, rising to -10 ° C, the The reactionsolution was poured into a mass percent concentration of 5percent hydrochloric acidin water hydrolysis reaction, pH value of the system 1, liquid separation, Theaqueous phase was extracted 100ml of toluene, and the combined organic phases, 100ml × 2 brine, net solvent was distilled off under reduced pressure, add 50mloil Ethers boil, cooled to room temperature, freezing in the refrigerator, awhite solid was filtered to give 16.2g (3-a), in 80percent yieldPreparation of 1-ethoxy-2, 3-difluorophenylboronic acid (T-3)According to the synthetic scheme shown above, compound (T-2) (129.5 g) obtained as an intermediate of was dissolved in DryTHF (500 ml), and the resultant solution was cooled to -70°C. In a nitrogen atmosphere, n-BuLi (500 ml) was added dropwise, and agitation was carried out at -70°C for 2 hours.The compound (T-2) obtained in the above step(129.5 g) was dissolved in Dry THF (500 ml)It was cooled to -70 ° C.N-BuLi (500 ml) was added dropwise under a nitrogen atmosphere, and the mixture was stirred at -70 ° C. for 2 hours. Thereafter, a Dry THF solution of trimethyl borate (129.5 g) was slowly added dropwise at -70 ° C., the temperature was raised to room temperature, and the mixture was stirred for 16 hours.After completion of the reaction, 2N HCl (200 ml) was added and the mixture was extracted with toluene, washed with water and saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a light brown solid.This product was recrystallized (heptane: toluene = 4: 1 by volume ratio) to obtain (T-20) as colorless crystals (117.2 g, yield 71percent).Under the protection of nitrogen, added to the reaction bottle 47.4 g 2, 3 - difluoro phenetole, 300 ml tetrahydrofuran, temperature control - 60 - - 70 °C dropwise 0.36 µM of n-butyllithium in hexane solution, then completing insulation reaction 1 hours, temperature control - 60 - - 70 °C dropwise 46.8 g of trimethyl borate, then naturally boxes to -30 °C. By adding 2 M hydrochloric acid aqueous solution 300 ml acidification, conventional post-processing, petroleum ether recrystallization to obtain a white solid (compound BYLC - 01 - 2) 53.9 g, HPLC: 99.8percent, yield 89percent(1) In a cryogenic container, add2.3-difluorophenethyl ether83.38 and 500(^ 1 'book, the process of feeding nitrogen protection, turn on cooling, cooling to -78 ~ 85 ° C, began dropping n-butyl lithium168.0g, plus finished -78 ~ 85 ° C insulation 2h, the control, the remaining 15.5percentBegin dropping of trimethyl borate 84.0g, the temperature was controlled at -75 ~ 85 ° C, after the addition was incubated at the end of stirring lh, sample testing, residual 2.5percentAfter the temperature was raised, 100.0 g of water was added to the vessel, and the mixture was suction filtered after removing THFThe crude product of 2.3-difluoro-4-ethoxyphenylboronic acid was 110.0 g and the HPLC purity was 98.5percent.
suzuki reaction
Computed Properties
Molecular Weight:201.97
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:202.0612806
Monoisotopic Mass:202.0612806
Topological Polar Surface Area:49.7
Heavy Atom Count:14
Complexity:182
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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B-(4-Ethoxy-2,3-difluorophenyl)boronic acid
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