2-CHLORO-4-FLUOROPHENYLBORONIC ACID
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2-CHLORO-4-FLUOROPHENYLBORONIC ACID
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CAS No:
313545-72-1
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Formula:
C6H5BClFO2
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Chemical Name:
2-CHLORO-4-FLUOROPHENYLBORONIC ACID
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Synonyms:
AKOS BRN-0714;2-CHLORO-4-FLUOROPHENYLBORONIC ACID;2-CHLORO-4-FLUOROBENZENEBORONIC ACID;2-Cholro-4-flurophenylboronic acid;2-Chloro-4-fluorobenzeneboronic acid 98%;2-Chloro-4-fluorobenzeneboronicacid98%;2-CHLORO-4-FUOROPHENYLBORONICACID;1-Borono-2-chloro-4-fluorobenzene
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CAS No:
Characteristics
40.5
0.15890
White Crystalline Powder
1.4±0.1 g/cm3
220-223
290.9°C at 760 mmHg
129.7±30.1 °C
1.533
Safety Information
IRRITANT
36/37/38-41-37/38
26-36/37/39-36-39-37
Xi
Irritant
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
2-CHLORO-4-FLUOROPHENYLBORONIC ACID Use and Manufacturing
To a 100 mL 3-necked round-bottom-flask were added 3-bromo-2-phenylimidazo[1 , 2-a]pyridin (3.28 g, 12.0 mmol), Intermediate A (90 mg, 0.38 mmol) and General procedure: A sealed tube was charged with 12a (134 mg, 0.4 mmol), 4-fluorophenylboronic acid (84 mg, 0.6 mmol), potassium carbonate (83 mg, 0.6 mmol), Pd(PPh3)4 (13 mg, 0.015 mmol) and THF(8 mL), The reaction mixture was stirred and refluxed at 90 C for 24 h under argon. After the reaction, it was diluted with EtOAc and filtrated by amorphous silica. The combined organic layer was washed by saturated brine. Then, it was dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (PE/EA = 4:1) and then recrystallized to afford the compound 8aa.In a vial 3-amino-4-bromo-2-methylpyrazole (0.20 g, 1.1 mmol), 2-chloro-4-fluorophenylboronicacid (0.30 g, 1.7 mmol) and sodium carbonate (2M) (2.3 ml, 4.6 mmol) were dissolved indioxane (2.5 ml). After degassing the resulting mixture for 10 min, tetrakis(triphenylphosphine)palladium (66 mg, 60 11mol) was added and it was stirred at 120 C20 for 1 h under microwave conditions. Solvents were removed and the crude material was purifiedby column chromatography (Si02, 0-100% EtOAc in PE) to obtain the title compound (97 mg, 38 %). 1 H NMR OH (500 MHz, CDCI3) 7.44 (s, 1 H), 7.31 (dd, J = 8.6, 6.1 Hz, 1 H), 7.24 (dd, J =8.5, 2.6 Hz, 1 H), 7.05 (ddd, J= 8.6, 7.9, 2.7 Hz, 1 H), 3.80 (s, 3H), 3.73 (br s, 2H). LCMS (Method25A): 2.70 min (226.2 m/z, MW).
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2-CHLORO-4-FLUOROPHENYLBORONIC ACID
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