Related Products of 17247-58-4, These common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, its 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.
A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7g (91 mmol) of sodium iodide in 150 mL of acetone wasrefluxed overnite and then cooled to rt. The inorganic solids were filtered off and the acetone and cyclopropylcarbinyl iodide (8.41g, 46%) distilled off at ambient and 150 torr at 80 C, respectively. A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30mL of anhydrous diethyl ether(Et20) cooled to-78 C was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyl lithium in cyclohexanes and the solution was stirred for 5 min. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110mL of hexanes cooled to-78 C, the mixture warmed to rt over 1 h and was then carefully concentrated in vacuo. This mixture was redissolved inEt20, washed once with some ice-cold water, dried(MgS04) and concentrated carefully. This mixture was redissolved in 30mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stirovernite. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount ofCH2Cl2 in hexanes with 1-2 drops of MeOH to afford 1.39 g(42%) of cyclobutyl carbinylsulfonamide as a whitesolid.’H NMR(CDCI3) 1.81-2. 03 (m, 4H), 2.14-2. 28 (m, 2H), 2.81-2. 92 (m,1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 3C NMR (CD3)8 19.10, 28.21, 30.64, 60.93 ; MS m/e 148(M-l)-. time: 1.73, method B), 818 (M++H).
Statistics shows that (Bromomethyl)cyclobutane is playing an increasingly important role. we look forward to future research findings about 17247-58-4.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary