3-BROMO-2-METHYL-BENZO[B]THIOPHENE

A solution of Br2 (2.10 mL, 6.55 g, 41.5 mmol, 1.02 equiv) inCHCl3 (60 mL) was slowly added to a solution of 5 (6.00 g, 40.8mmol, 1.00 equiv) in CHCl3 (300 mL) over 5 h at r.t. The mixturewas stirred for 15 h at r. t., quenched with sat. aq Na2SO3 (50mL), and extracted with CH2Cl2 (4 × 100 mL). The combinedorganic layers were washed with sat. aq NaCl (2 × 100 mL), dried over Na2SO4, and the solvents were removed in vacuo.Purification by flash chromatography (silica, hexane) gave 6 asa colourless solid in 96percent yield (8.68 g, 38.2 mmol). TLC (SiO2, hexane): Rf = 0.25. 1H NMR (400 MHz, DMSO-d6): δ = 8.00–7.94(m, 1 H), 7.68–7.63 (m, 1 H), 7.51–7.38 (m, 2 H), 2.54 (s, 3 H) ppm. 13C NMR (101 MHz, DMSO-d6): δ = 137.62, 136.57, 135.65, 125.38, 125.14, 122.75, 121.92, 105.78, 15.17 ppm. MS (EI): m/z[M] + calcd for C9H7BrS: 225.9448; found: 225.9446.Under ice-water bath conditions, the compound of formula 3 (2.67 g, 18 mmol)As raw materials dissolved in acetic acid, stirring slowly and evenly addedBromosuccinimide (3.20 g, 18 mmol) was added and the reaction was continued for an additional 24 h with an ice bath. The reaction was quenched with water and the organic phase and the aqueous phase were separated. The aqueous phase was neutralized with sodium hydroxide and extracted with methylene chloride , Before and after the merger of the organic phase, then saturatedSodium carbonate solution three times, dried over anhydrous sodium sulfate, Silica gel column chromatography with petroleum ether to give 3.52 g of a white solid, Yield: 86percent.Compound 5b was prepared by an analogous methodsimilar to that used for 5a and obtained as a light yellow liquid in 55percent yield.1.06 g of 3-Bromo-benzo[b]thiophene (5.0 mmol) is dissolved in 10ml of dry tetrahedrofuran and cooled to -78

Molecular Weight:227.12
XLogP3:4
Hydrogen Bond Acceptor Count:1
Exact Mass:225.94518
Monoisotopic Mass:225.94518
Topological Polar Surface Area:28.2
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes