Acetyl chloride → 3-Bromo-2,2-dimethylpropyl acetate

Participants

Reaction Steps

To a mixture of 3-bromo-2,2-dimethyl-1-propanol (5 mL) and triethylamine (15 mL) was added tetrahydrofuran (50 mL), acetyl chloride (3.8 mL) was added dropwise under ice-cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give acetic acid (3-bromo-2,2-dimethyl-1-propyl)ester (8.37 g). The obtained acetic acid (3-bromo-2,2-dimethyl-1-propyl)ester (8.37 g) were added sodium sulfite (5.05 g) and water (20 mL), and the mixture was stirred with heating under reflux for 20 hr. To the reaction mixture was added concentrated hydrochloric acid (5.81 mL), and the mixture was stirred with heating under reflux for 1 hr. The reaction mixture was cooled, neutralized with 4N aqueous sodium hydroxide solution (20.5 mL), and the mixture was concentrated to about 10 mL. The precipitated precipitate was collected by filtration, and the filtrate was concentrated. To the obtained residue was added phosphorus pentachloride (18.35 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Into the reaction mixture was poured ice water, and the mixture was extracted with dichloromethane. The solvent was evaporated from the organic layer to give crude 3-chloro-2,2-dimethylpropane-1-sulfonyl chloride (3.99 g). Using the obtained crude 3-chloro-2,2-dimethylpropane-1-sulfonyl chloride (3.99 g) and ethyl 4-aminobenzoate (3.21 g) and by the reaction and treatment in the same manner as in Preparation Example 17, the title compound (127 mg) was obtained.

Provenance & Evidence