Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 609-12-1
General procedure: Benzenesulfonamide (1.2mmol), ethyl alpha-bromophenylacetate or ethyl pheny-lacetate (2.4mmol), and toluene (4mL)werecombinedinasealedtubeequippedwith astirbar.Themixturewasstirredat50Cfor10min,TiCl4 (1.8 mmol) was added, andthereactionmixturewasheatedto115C.Afteravariableperiodoftimethe mixturewasdilutedwithH2O (10mL)toremovetheexcessofTiCl4, filtered,andextracted withAcOEt(3¡Á15mL). The combined organic layers were dried over anhydrous Na2SO4 and thesolventwasevaporatedinvacuo.Crudecompoundswere purified by flash column chromatography (silicagel;cyclohexane=AcOEt 8:2). 2-Bromo-N-[(4-methoxyphenyl)sulfonyl]-3-methylbutanamide (4c). Sticky oil, 59% yield; IR(KBr) 3564, 3236, 2970, 1906, 1722, 1596, 1499, 1443, 1346, 1265, 1165, 1087, 1023, 865, 834,559 cm-1; 1H NMR (CDCl3) d 0.94 (d, 3H, J 6.3Hz, CH3), 0.95 (d, 3H, J 6.6 Hz, CH3), 2.19(octuplet, 1H, J 6.6 Hz, CH3CHCH3), 3.87 (s, 3H, OCH3), 4.09 (d, 1H, J 6.6 Hz, CHBr), 6.99 (d,2H, J 9.0 Hz, CH Ar), 8.00 (d, 2H, J 9.6 Hz, CH Ar), 9.09 (broad s, 1H, NH); 13C NMR (CDCl3)d 18.9 and 20.2 (CH3), 32.4 (CH3CHCH3), 55.7 (OCH3), 58.0 (CHBr), 114.1 (CH Ar), 129.0 (CSAr), 130.9 (CH Ar), 164.1 (CH3OC Ar), 166.2 (CONH); Anal calcd for C12H16BrNO4S: C 41.15; H4.60; N 4.00; found C 41.22; H 4.59; N 4.02 %.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.
Reference:
Article; Ammazzalorso, Alessandra; Tricca, Maria Luisa; Bruno, Isabella; De Filippis, Barbara; Di Matteo, Mauro; Fantacuzzi, Marialuigia; Giampietro, Letizia; Maccallini, Cristina; Mollica, Adriano; Amoroso, Rosa; Synthetic Communications; vol. 45; 22; (2015); p. 2546 – 2554;,
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