Related Products of 10485-09-3, The chemical industry reduces the impact on the environment during synthesis 10485-09-3, name is 2-Bromoindene, I believe this compound will play a more active role in future production and life.
A solution of (pS)-9 (2.00g, 4.04mmol) in THF (70mL) was cooled to -78C, treated with nBuLi (1.6M in hexanes, 3.03mL, 4.85mmol) and stirred at -78C for 30min. A solution of ZnCl2 (0.5M in THF, 9.70mL, 4.85mmol) was added dropwise, the solution warmed to rt over 30min and stirred at rt for 1h. Next, Pd(PPh3)2Cl2 (0.140g, 0.200mmol) in THF (5mL) was treated with DIBAL (1M in THF, 0.400mL, 0.440mmol), stirred for 5min and added dropwise via cannula to the reaction. The resultant solution was heated at reflux and a solution of 2-bromoindene42 (1.56g, 8.08mmol) in THF (5mL) added dropwise over 30min. After refluxing for 4d the solution was cooled to rt, quenched with NH4Cl(aq) (10mL), washed with water (2×40mL), brine (40mL), dried over MgSO4 and concentrated in vacuo. Purification was achieved using flash column chromatography (pet. ether) to give the title compound as an orange oil (1.47g, 75%). Rf=0.31 (pet. ether); [alpha]25D=+235.3[alpha]D25=+235.3 (c 1.02, CHCl3); IR numax 2943, 2866, 1461, 1391, 1130, 1105, 1057, 999, 908, 882cm-1; 1H NMR (400MHz) delta 1.18-1.70 (21H, m, Si(iPr)3), 3.72 (1H, d, J=22.8, IndCH2), 3.79 (1H, d, J=22.8, IndCH2), 4.07 (5H, s, Cpunsub), 4.26 (1H, app t, J=2.5, Cpsub), 4.42 (1H, dd, J=2.5, 1.5, Cpsub), 4.48 (1H, dd, J=2.5, 1.5, Cpsub), 4.74 (1H, d, J=11.6, CpCH2), 4.95 (1H, d, J=11.6, CpCH2), 7.08 (1H, s, IndCH), 7.16 (1H, app dt, J=7.2, 0.8, ArH), 7.25 (1H, app t, J=7.2, ArH), 7.31 (1H, d, J=7.2, ArH), 7.45 (1H, d, J=7.2, ArH); 13C NMR (100MHz) delta 12.2 (CH), 18.2 (CH3), 41.0 (CH2), 61.4 (CH2), 67.3 (CH), 69.0 (CH), 69.7 (CH), 70.9 (CH), 81.4 (C), 85.0 (C), 120.1 (CH), 123.4 (CH), 123.8 (CH), 126.4 (CH), 126.6 (CH), 142.7 (C), 145.5 (C), 146.2 (C); m/z (EI+) 510 (10%, M++HNa), 509 (26%, M++Na), 314 (23%, M++H-OTIPS), 313 (100%, M+-OTIPS), 301 (15%, M+-COTIPS), 269 (7%); HRMS C29H38FeNaOSi calcd 509.1934, found 509.1903; Anal. Calcd for C29H38FeOSi: C, 71.59; H, 7.87. Found: C, 71.10; H, 7.81.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromoindene, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Anderson, James C.; Grounds, Helen; Szaloki, Gyoergy; Tetrahedron Asymmetry; vol. 24; 17; (2013); p. 1023 – 1034;,
Bromide – Wikipedia,
bromide – Wiktionary