Bromination and Iodination of Some p-Alkylbenzoic Acids

Total Synthesis of Pulchrol and Pulchral

“…化合物 5 的合成很容易由对苯二酚 3 通过单甲基化 [8] 、羧化和 酯化 [9] 制备. 对甲基苯甲酸 6 进行邻溴化和酯化反应 [10] , 两步反应得到化合物 7, 收率为 71%. 化合物 7 经甲基 自由基溴化 [11] 得到 3-溴-4-溴甲基苯甲酸甲酯(8), 用 DIBAL-H 还原得到(3-溴-4-溴甲基)苯甲醇(9), 收率为 95%, 该醇羟基保护得到醚 10, 产率 85%.…”

“…1 [9] , 收率 78% (两步). 1 [10] , 收率 71%(两步). 1 H NMR (400 MHz, CDCl 3 ) δ: 8.16 (d, J＝1.6 Hz, 1H), 7.83 (dd, J＝7.9, 1.7 Hz, 1H), 7.26 (d, J＝7.9 Hz, 1H), 3.89 (s, 3H), 2.41 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 165.…”

Synthesis of benzocarbacephem and benzocarbapenem derivatives by copper-promoted intramolecular aromatic substitution

“…); v,,,,(KBr) 3 450, 1755, and 1 685 cm-'; 6,(D2O) (as sodium salt)1.61(lH,m),2.37(1H,m),2.91(2H,m),2.92(1H,dd,J2 and 15.5 Hz), 3.38 (1 H,dd,J4.5 and 15.5 Hz),3.87 (1 H,m),m); m/z 217 ( M ' ) , 175,130,73,60,.-This compound was obtained in a manner similar to the procedure for the preparation of acid (Ha), as a solid (7.6 mg), m.p. 175 "c; v,,,.(KBr) 1 755 and 1 688 cm-'; 6,(D20) (as sodium salt) 1.76 (1 H,dddd,J 2.5,12.5,15,and 41.5 Hz),2.70 ( I H,dddd,J2.8,2.8,12.5,and 15 Hz),2.95 (1 H,dd,J 2 . 5 and 15.5 Hz),3.42 (1 H,dd,J 4 .…”

The synthesis of 3‐hydroxymethyldibenzo[b,f]thiepin 5,5‐dioxide, a prostaglandin antagonist

“…The precipitate was collected, washed with water and dried. The solid was dissolved in hot ethanol (2 litres), filtered to remove cuprous iodide and the filtrate crystallised by addition of water (1.5 litres) to give 255 g (61%) of the iodo compound 3 mp 204-206' (lit [18] mp 205.206'); hplc solvent 1, Rt 12.1 minutes, 96%; Rt 9.9 minutes 3 % chloro compound. A mixture of the bromo compound 2 (1 kg, 4.65 moles), thiophenol (499 ml, 4.86 moles) and cuprous oxide (352 g, 2.46 moles) in quinoline (2.2 litres) was heated (nitrogen atmosphere) to 180'.…”