Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4415-82-1, name is Cyclobutylmethanol. This compound has unique chemical properties. The synthetic route is as follows. 4415-82-1
Step 1. 4-Bromo-5-(cyclobutylmethoxy)-2-nitroaniline Sodium hydride (0.82 g, 60% w/w, 20 mmol) was added at 0 C. to a solution of cyclobutyl/methanol (1.8 mL, 20 mmol) in THF (40 mL). The 0 C. bath was removed, and the reaction mixture was stirred for 30 min. The reaction mixture was again cooled to 0 C. with an ice bath, and 4-bromo-5-fluoro-2-nitroaniline (2.5 g, 11 mmol) was added. The ice bath was removed, and the reaction mixture was stirred for 18 h at room temperature. The reaction was quenched with sat. NH4Cl and then diluted with H2O. The aqueous solution was extracted with EtOAc (125 mL), and the organic layer was separated and washed with brine (100 mL). The resulting organic layer was dried over MgSO4, filtered, and concentrated. Recrystallization from CH2Cl2/hexanes upon cooling at 0 C. overnight afforded the title compound as a red-brown solid (2.3 g, 72%). 1H NMR (300 MHz, CDCl3) delta 8.28 (d, J=1.0 Hz, 1H), 6.07 (s, 1H), 3.90 (d, J=6.0 Hz, 2H), 2.88-2.61 (m, 1H), 2.09 2.25-2.00 (m, 2H), 2.01-1.71 (m, 4H). LCMS calculated for C11H14BrN2O3 (M+H)+: m/z=301.0, 303.0. found: 301.1, 303.1.
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Reference:
Patent; Incyte Corporation; Yue, Eddy W.; Combs, Andrew P.; Buesking, Andrew W.; US2015/148375; (2015); A1;,
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