3-Bromobenzenesulfonyl fluoride

To a stirred solution of 3-bromophenylsulfonyl chloride (5 g, 0.0196 mol) in acetonitrile (20 ml) was added potassium fluoride (2.27 g, 0.0391 mol) followed by 18-crown-6 ether (0.08 g) and the reaction stirred at room temperature for 18 h. The reaction mixture was then washed with water (60 ML), extracted with ethyl acetate (3 x 80 ml) and the combined organic extracts dried (NA2SO4). Solvents were EVAPORATED IN VACUO to give a yellow oil (3.79 g, 81 percent). 'H NMR (CDCI3) : 8 7.55 (1H, t), 7.92 (1H, d), 7.95 (1H, d), 8.14 (1H, s).General procedure: A round bottom flask was charged with 4-bromobenzenesulfonyl fluoride 1a (1 equiv), B2(pin)2 (1.1 equiv), Pd(dppf)Cl2CH2Cl2 (3 mol %) and KOAc (3 equiv), evacuated and back-filled with N2 three times. Degassed anhydrous 1, 4-dioxane (0.33 M) was added and the reaction was stirred at 80 C for 16 h, then cooled to ambient temperature and concentrated in vacuo. The mixture was diluted with EtOAc, washed sequentially with water and brine, dried with anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography rapidly to afford the corresponding benzenesulfonyl fluoride boronic acid pinacol ester.General procedure: To a Schlenk tube equipped with a stirrer, 4-biphenylsulfonyl fluoride (23.6 mg, 0.10 mmol) was added at room temperature, Tris (trimethylsilyl) amine (70.1 mg, 0.30 mmol, 1.5 equiv.) In DMF (0.50 mL) was charged, After cooling to 0 C., P4-tBu base (37.5 muL, 0.030 mmol, 0.30 equiv.) Was added thereto.Trifluoromethane (excess) was then bubbled through for 1 minute After that, the reaction was carried out at the same temperature for 7 hours.After completion of the reaction, a saturated ammonium chloride aqueous solution was added, The organic layer was extracted with methylene chloride, the obtained organic layer was washed with a saturated sodium chloride aqueous solution, After drying over thorium, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography Purification by column chromatography gave 4- (trifluoromethylsulfonyl) biphenyl (3) as a target product in a yield of 84%.

Molecular Weight:239.06
XLogP3:2.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:237.90994
Monoisotopic Mass:237.90994
Topological Polar Surface Area:42.5
Heavy Atom Count:11
Complexity:221
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes