1-Acetoxy-2-bromoethane → HCID 59389289, compound

Participants

Reaction Steps

60% sodium hydride (162 mg) was added to a solution of the compound of Example 183 (700 mg) in N,N-dimethylformamide (40 mL) in a stream of argon gas while the solution was stirred in an ice bath. The mixture was then stirred at room temperature for 15 min. Subsequently, bromoethyl acetate (597 μL) was added to the mixture under stirring in an ice bath. The mixture was further stirred at room temperature for 3 hours. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water (×2) and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification by silica gel column chromatography (hexane:ethyl acetate=2:1) gave the title compound as a mixture with o-alkylated form. This mixture was dissolved in 47% hydrobromic acid (20 mL) and the solution was stirred at 130° C. for 1 hour. After cooling, a 20% aqueous potassium hydroxide solution was added to make the mixture basic. The resulting crystals were separated by filtration and diluted hydrochloric acid was added to the filtrate to make it acidic. The filtrate was then extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the title compound as a yellow amorphous material (490 mg).

Provenance & Evidence