Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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. SDS of cas: 1871-57-4
To a cold (-78 C, acetone/solid CO2) and magnetically stirred solution of diisopropylamine (0.8 mL, 5.7 mmol) in anhydrous THF (15 mL) under an argon atmosphere, a solution of n-BuLi in hexanes (2.3 mL, 2.5 M, 5.7 mmol) was added dropwise.When n-BuLi addition was finished, the solution was allowed to warm to 0 C for 1 h, it was cooled again to -78 C, and a solution of 11 (690 mg, 2.38 mmol) in anhydrous THF (8 mL) was added dropwise. Then, the solution was stirred a -78 C for 15 min and allowed to warm to 0 C for 1 h. The solution was again cooled to -78 C and 3-chloro-2-(chloromethyl)-1-propene (0.36mL 96% content, 373 mg, 3.0 mmol) was added dropwise. The reaction mixture was allowed towarm to room temperature and it was stirred for 3 days at this temperature. The mixture was made acidic with aqueous 1N HCl (10 mL) and was extracted with Et2O (3¡Á50 mL). The combined organic extracts were dried (anhydrous Na2SO4) and concentrated in vacuo to give abrown waxy residue (960 mg) that was subjected to column chromatography (silica gel 35-70mum, 30 g, hexane/EtOAc mixtures) to give on elution with hexane/EtOAc 9:1, product 12 (515mg, 63% yield) as a yellow solid. Rf 0.51 (silica gel, 8 cm, hexane/EtOAc 8:2); mp 190-192 C (from EtOAc/hexane); IR (ATR, numax, cm-1): 1770w and 1693s (C=O st); 1H NMR (400 MHz,CDCl3) delta 1.65 (br s, H2O), 2.11 [dt, 2JHH 16.4 Hz, 4JHH 2.4 Hz, 2H, 16(18)-Hn], 2.47 (s, 3H, NCH3),2.64 [br d, 2JHH 16.4 Hz, 2H, 16(18)-Hx], 4.51 [s, 2H, 4(9)-H], 4.61-4.62 (br s, 2H,C17=CH2), 7.06-7.10 [m, 2H, 6(7)-H], 7.17-7.20 [m, 2H, 12(13)-H], 7.21-7.25 [m, 2H, 5(8)-H], 7.34-7.38 [m, 2H, 11(14)-H]; 13C NMR (100.6 MHz, CDCl3) delta 24.5 (CH3, N-CH3), 39.3[CH2, C16(18)], 49.5 [CH, C4(9)], 62.0 [C, C3a(9a)], 108.8 (CH2, C17=CH2), 124.9 [CH,C5(8)], 126.6 [CH, C11(14)], 126.81 [CH, C12(13)], 126.85 [CH, C6(7)], 139.6 [C, C4a(8a)],139.9 [C, C10(15)], 146.6 (C, C17), 180.1 [C, C1(3)]; HRMS (ESI-TOF): calcd. for[C23H19NO2+H]+: 342.1489. Found: 342.1485; Anal. calcd. for C23H19NO2¡¤0.25H2O: C, 79.86;H, 5.68; N, 4.05%. Found: C, 79.47; H, 5.62; N, 3.88%.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1871-57-4, its application will become more common.
Reference:
Article; Camps, Pelayo; Gomez, Tania; Otermin, Ane; ARKIVOC; vol. 2014; 2; (2014); p. 103 – 119;,
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