4-Iododibenzothiophene

off-white powder

General procedure: To a stirred, cooled (0 °C) solution of 2, 2, 6, 6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2–3 mL) were successively added ca. 1.6M BuLi in hexanes (1.5 mmol) and, after 5 min, ZnCl2·TMEDA35 (0.13g, 0.50 mmol). The mixture was stirred for 15 min at 0 °C before introduction of xanthone (1a, 0.20 g, 1.0 mmol). After 2 h at this temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before the addition of aq sat. Na2S2O3 soln (4 mL). The mixture was extracted with EtOAc (3 × 20 mL) and the combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by chromatography (silica gel, heptane/CH2Cl2 100:0 to 80:20) afforded the products.400 mL of tetrahydrofuran in a round bottom flask containing a dibenzothiophene 50 g (271 mmol) then gave the put under a nitrogen atmosphere the temperature was adjusted to -78 . N-butyllithium was added dropwise slowly to 178 mL (285 mmol) after 30 min, was added slowly dropwise to iodine 69 g (271 mmol), after 12 hours, raising the temperature to room temperature. 2 hours stirring it binds the sodium thiosulfate solution. Extracts were evaporated under reduced pressure and the organic layer collected. Filtering the resulting solid was recrystallized with hexane to obtain a compound represented by [Intermediate 4-a] 52.1 g (yield 60percent).After 400mL of tetrahydrofuran gave put dibenzothiophene 50g (271 mmol) in a round bottom flask containing a nitrogen atmosphere the temperature was adjusted to -78 °C. After 30 minutes, slowly added dropwise n-butyl lithium to 178 mL (285 mmol) was then slowly added dropwise to iodine 69 g (271 mmol) after 1 h, warming to room temperature. After stirring for 24 hours it binds the aqueous solution of sodium thiosulfate. Extracts were evaporated under reduced pressure and the organic layer collected. And the resulting solid was recrystallized with heptane and filtered to give a dry 52 g. (60percent yield)Dibenzothiophene (20 g, 0.109 mol, Sigma Aldrich), N-Iodosuccinimide (12.1 g, 0.054 mol, Sigma Aldrich)And Solvent Chloroform / Acetone (3: 1), and the mixture was reacted at 25 ° C with stirring. After cooling the reaction mixture, the crude product was added by the amount of the reaction solvent, and after the extraction, column purification (n-Hexane) was conducted to obtain 9 g (yield: 27percent) of Intermediate 1-5.Apparatus set-up: (0336) A 10 L 3 -necked round-bottomed flask, equipped with a mechanical overhead stirrer, nitrogen inlet and exhaust. (0337) Experimental Procedure: (0338) Dibenzothiophene (300 g, 1.628 mol) was taken in dry tetrahydrofuran (5 L). The reaction mixture was cooled to - 40 °C using dry ice/ acetonitrile bath. n-BuLi (651 mL, 2.5 M in hexane) was added drop wise slowly. (0339) The reaction mixture was stirred at 0 °C to -10 °C for 5 hours, then cooled to -78 °C and iodine (454 g, 1.7908 mol) was added portion wise slowly. (0340) The reaction mixture was slowly allowed to room temperature and stirred for 16 hours. (0341) The reaction mixture was quenched with water (500 mL) and extracted with ethyl acetate (2 x 1 L). (0342) The combined organic phase was washed with sodium thiosulphate solution (2 L), water (1 L), brine (1 L), dried over sodium sulphate and concentrated (370 g). The crude product was purified by hot acetonitrile crystallization to get 300 g of intermediate 2 with 98.75percent HPLC purity. (0343) 1H-NMR (400 MHz. COCh): δ [ppm] δ 7.20- 7.24 (m, IH), 7.49-7.55 (m, 2H), 7.84 (dd, 7 = 0.8 Hz, 7.6 Hz, IH), 7.89-7.93 (m, IH), 8.10-8.14 (m, IH), 8.18 (dd, = 0.8 Hz, 8.0 Hz, IH).

Molecular Weight:310.15
XLogP3:5
Hydrogen Bond Acceptor Count:1
Exact Mass:309.93132
Monoisotopic Mass:309.93132
Topological Polar Surface Area:28.2
Heavy Atom Count:14
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes