A common heterocyclic compound, the benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one,cas is 19932-85-5, mainly used in chemical industry, its synthesis route is as follows.,19932-85-5
General procedure: IV, e.g. bromo-substituted 3H-1,3-benzoxazol-2-one, (1 eq.) was suspended in a 1:1 toluene/EtOH mixture (10 mL per mmol IV). The boronic acid V (1.5 eq.) was added followed by aq. NaCO3 (2 M, 0.55 mL per mmcl IV, 1.1 eq.). The resulting suspension was degassed undernitrogen for 10 mm, followed by addition of Pd(PPh3)4 (0.1 eq.) and heating under microwave irradiation at 100 C for 30 mm. The reaction mixture was diluted with EtOAc (40 mL per mmcl IV), and water (40 mL per mmcl IV) was added. The two phases were separated and the aqueous layer was extracted with EtOAc (2 x 40 mL per mmcl IV). The combined organic phases were dried over Na2SO4, evaporated on silica, and the compound was purified by column chromatography using the Teledyne ISCO apparatus (cyclohexane:EtOAc).The title compound was obtained according to the General Procedure II, starting from 6-bromobenzoxazolone (500 mg, 2.34 mmol) and (4-fluorophenyl)boronic acid (490 mg, 3.50mmol). White solid (450 mg, 42%). 1H NMR (400 MHz, CDCI,) 6 7.08 (m, 3H), 7.33 (dd, J = 8.1, 1.6 Hz, 1H), 7.39 (d, J = 1.4 Hz, 1H), 7.47 -7.52 (m, 2H), 7.91 (s, 1H). MS (ESI) m/z: 228 [M-H].
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Reference£º
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; PIZZIRANI, Daniela; BACH, Anders; SCARPELLI, Rita; MELZIG, Laurin; MOR, Marco; (72 pag.)WO2015/173169; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem