3-Bromo-1-benzothiophene

Colorless to yellow to red liquid

General procedure: PdClTo a solution of benzo[b]thiophene (10 g, 74.5 16 mmol) in chloroform (75 mL) and acetic acid (75 mL), was stepwise added NBS (16.6 g, 93.268 mmol) for 4 hr at 0°C and the mixture allowed to stir at room temperature for 48 hr. The progress of the reaction was monitored by TLC and, after completion of reaction, the reaction mass was diluted with chloroform (200 mL) and the resulting mixture was successively washed with a saturated solution of sodium thiosulfate (200 mL), sodium carbonate (200 mL) and brine (150 mL). The extracted organic layer was then dried over sodium sulfate, filtered and evaporated under reduced pressure. The resulting red liquid was then filtered of a pad of silica gel, eluting with hexane to afford 3-bromo-1-benzothiophene (15.87 g, 74.474 mmol, 100percent) as yellow oil. The ‘H NMR and mass was confirmed by reported literature.Benzo [b] thiophene 30 g (0.224 mol)225 mL of CHCl3 and 225 mL of AcOH were added at room temperature. 43.8 g (0.246 mol) of N-Bromosuccinimide was added to the reaction solution, and the mixture was heated to reflux for 3 hours. The reaction mixture was cooled to 0 [deg.] C and neutralized with a saturated aqueous solution of NaHCO3 to terminate the reaction. The organic layer was separated with 500 mL of CH3Cl and washed with distilled water and brine. The obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and then purified by silica gel column chromatography to obtain the aimed compound (45.3 g, yield 95percent).Benzothiophene (2.68 g, 20.0 mmol) was dissolved in glacial acetic acid (100 mL) and cooled to 0° C. The resulting solution was treated by dropwise addition of bromine (1.08 mL, 21.0 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. The crude mixture was concentrated to an oil. The residue was purified by silica gel chromatography eluting with hexane to obtain 4.02 g (94percent) 3-bromobenzothiophene.Weigh benzothiophene (1.34 g, 10 mmol), N-bromosuccinimide (1.78 g, 10 mmol) was added to a three-necked flask and 20 mL of carbon tetrachloride was added.Irradiate with a 200w incandescent bulb and react at room temperature for 2 hours.The white solid was filtered off and the liquid was concentrated.1.9 g (90percent) of a colorless transparent liquid were obtained.A 2 L round bottom flask was charged with benzo[b]thiophene (50 g, 373.13 mmol), CHTo a solution of benzo[b]thiophene (6.91 g, 51.5 mmol) in DMF (100 mL) was addedN-bromosuccinimide (8.71 g, 48.9 mmol) at 0 °C, and the mixture was allowed to warm up to25 °C and stirred for 9 h. Into the reaction mixture was added saturated aq. Na2SO3 (50 mL).The resulting mixture was extracted with hexane (3 × 100 mL) and the combined organic phasewas washed with water (3 × 100 mL) and brine (100 mL). The organic phase was dried overMgSO4, filtered, and concentrated under reduced pressure. The crude product was purified bycolumn chromatography on silica gel (hexane) to afford the title compound as colorless liquid(9.23 g, 43.3 mmol, 84percent).Benzo[b]-thiophene (10 g, 74.5 mmol) was dissolved in AcOH/CHClBenzo on L reactor thiophene 35 g (261 mmol), was stirred into 350 mL of tetrahydrofuran. 0 And cooled to ° C, were introduced into N-bromo-succinimide 55.7 g (313 mmol) and stirred for 1 hour. After the temperature was raised to roomtemperature and stirred for 12 hours, into a sodium sulfite aqueous solution and then Imohsel using ethyl acetate and distilled water and the organic layer was extracted. Theorganic layer was concentrated under reduced pressure to give the intermediate 14-b43 g (yield: 63.4percent).EXAMPLE 5

Molecular Weight:213.10
XLogP3:3.8
Hydrogen Bond Acceptor Count:1
Exact Mass:211.92953
Monoisotopic Mass:211.92953
Topological Polar Surface Area:28.2
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes