2-PHENYL-ETHANESULFONYLCHLORIDE

General procedure: The appropriate phenylethyl bromide 2 (a–g) (1 mmol) was dissolved in MeCN (2 mL) and KSAc (114 mg, 1 mmol) was added in an ice-bath. After stirring for 1 h, 1 mL of HCl conc. was added followedby the slow addition of NaClO2 (360 mg, 4 mmol). Theobtained mixture was stirred for 40 min and then the reactionwas quenched adding water (3 mL). The resulting solution wasevaporated in vacuum to remove the solvent, extracted with EtOAc(3 10 mL) and dried over anhydrous Na2SO4. Finally, the solution was concentrated in vacuum to obtain the desired compounds 3(a–g).General procedure: Step 1. An alkyl halide or mesylate (5 mmol) and thiourea (0.381 g, 5 mmol) wererefluxed in 5 mL of ethanol for 1 h. After removal of the solvent in vacuum thecorresponding S-alkyl isothiourea salt was obtained as white solid or sticky oil.Step 2. A 50 mL three-necked flask equipped with a thermometer and asolid-addition funnel was immersed in an ice-bath. To the flask was sequentiallyadded NaClO2 solid (for isothiouronium chlorides or sulfonate, 1.61 g, 15 mmol; forisothiouronium bromides, 2.14 g, 20 mmol, 85percent purity), MeCN (10 mL), and thenconc. HCl (for isothiouronium chlorides or sulfonate, 3 mL; for isothiouroniumbromides, 4 mL) during 1 min at such a rate that the inner temperature was maintainedless than 10 °C. Then S-alkyl isothiourea salt was slowly added througth the solidaddition-funnel to keep the inner temperature less than 20 °C. After the addtion, theresulting mixture was stirred for another 30 min. Then 25 mL of water was added, and the resultant mixture was evaporated in vacuum at 15 °C to remove acetonitrile. Afteraddition of 100 mL of water, the solid products were obtained by filtration on aBuchner funnel and dried under an infrared lamp, while the liquid products wereobtained by extraction with 15 mL of ethyl acetate, drying with Na2SO4, andconcentration in vacuum.For 1, 4-dibromobutane, the amounts of thiourea, NaClO2 solid, MeCN, and conc.HCl were doubled.

Molecular Weight:204.67
XLogP3:2.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:204.0011784
Monoisotopic Mass:204.0011784
Topological Polar Surface Area:42.5
Heavy Atom Count:12
Complexity:212
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes