4-Toluenesulfonyl chloride → HCID 18411857, compound

Participants

Reaction Conditions

Reaction Steps

1.02 g of p-toluensulfonyl chloride (5.35 mM), 1.24 ml of diisopropyl ethylamine (7.13 mM) and 86 mg of 4-(dimethylamino)pyridine (0.71 mM) were added to the reaction solution (3.57 mM) containing 500 mg of 2-(2-fluoro-phenyl)-ethanol (3.57 mM) dissolved in methylene chloride solution with stirring for 6 hrs at 0° C. under Ar atmosphere, and then the reaction mixture was stirred for 12 hrs at room temperature. The resulting mixture was neutralized with ammonium chloride, extracted with ethyl acetate and washed with saturated NaCl solution to separate into an organic layer and water layer. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:7) as an eluant to give 740 mg of toluen-4-sulfonate-2-(2-fluoro-phenyl)-ethyl ester (u) (yield: 70%).

Provenance & Evidence