Reaction #2028879

Reaction equation

alcohol

4-[3-hydroxymethyl-5-phenyl-1H-pyrazol-1-yl]benzene Sulfonamide

diethylaminosulfur trifluoride

→

4-[3-fluoromethyl-5-phenyl-1H-pyrazol-1-yl]benzenesulfonamide

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherpartitioned between water and dichloromethane
2. 2
   WashThe organic solution was washed with brine
3. 3
   Concentrationconcentrated
4. 4
   OtherThe residue was chromatographed on silica (72 mg, 34%)

Procedure

To a mixture of the alcohol from Step 3 (212 mg, 0.64 mmol) in dichloromethane (4 mL) was added diethylaminosulfur trifluoride (0.13 mL, 1.0 mmol). The reaction mixture was stirred at room temperature for 3 hours and partitioned between water and dichloromethane. The organic solution was washed with brine and concentrated. The residue was chromatographed on silica (72 mg, 34%): mp 162°-163° C.; Anal. calc'd for C16H14N3O2SF: C, 58.00; H, 4.26; N, 12.68. Found: C, 57.95; H, 4.03; N, 12.58.

Source