Boron Trichloride → HCID 58896047, compound

Participants

Reaction Conditions

Reaction Steps

Boron trichloride solution (145 mL, 1.0 M in CH2Cl2) was added dropwise to a solution of N-(3,5-Dimethoxy-phenyl)-N-heptyl-4-methyl-benzenesulfonamide (19.0 g, 47 mmol) and tetrabutylammonium iodide (53.5 g, 145 mmol) in 250 mL of anhydrous dichloromethane at −78° C. under argon atmosphere. The reaction mixture was stirred at −78° C. for 20 minutes, and then at 0° C. for 2 h. The reaction was quenched by addition of 100 mL of water slowly. The organic layer was separated and washed with water, 30% aqueous NaHSO3 solution, water and brine, and dried over anhydrous sodium sulfate. Removal of solvent and drying reagent provided 50.83 g of a semi-solid crude product. This material was chromatographed on silica gel column eluted with a mixture of petroleum ether and acetone (2:1) to afford 16.83 g (94.6%) of the title compound as a light yellow solid.

Provenance & Evidence