Reaction #2028892

Reaction equation

compound

4-[4-bromomethyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

collidine

dimethyl sulfoxide

→

desired product

Yield 66.0%

4-[4-formyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

Yield 66.0%

Conditions

Workup

1. 1
   OtherThe reaction solution was partitioned between ethyl acetate and water
2. 2
   Washthe organic solution was washed with water
3. 3
   Otherdried
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was chromatographed (1:1 hexane:ethyl acetate)

Procedure

To a solution of the compound prepared in Step 1 (362 mg, 0.79 mmol) in dimethyl sulfoxide (7 mL) was added collidine (0.14 mL, 1.0 mmol). The solution was heated at 120° C. for 3 hours and then kept at overnight at room temperature. The reaction solution was partitioned between ethyl acetate and water and the organic solution was washed with water, dried and concentrated. The residue was chromatographed (1:1 hexane:ethyl acetate) to give the desired product (205 mg, 66%).

Source