4-Toluenesulfonyl chloride → HCID 18411857, compound

Temperature

0 °C

1.02 g of p-toluenesulfonyl chloride (5.35 mM), 1.24 ml of diisopropyl ethylamine (7.13 mmol) and 86 mg of 4-(dimethylamino)pyridine (0.71 mmol) were added to the reaction solution (3.57 mmol) containing 500 mg of 2-(2-fluoro-phenyl)-ethanol (3.57 mmol) 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%).

1. stirringthe reaction mixture was stirred for 12 hrs at room temperature
2. extractionextracted with ethyl acetate
3. washwashed with saturated NaCl solution
4. customto separate into an organic layer and water layer
5. dry with materialThe organic layer was dried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
9. additionmixed with methanol and chloroform (1:7) as an eluant

ORD record

ord-6c20010047b14e1c80c8edc3bf729987

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846963B2