4-Bromophenol → HCID 10915466, compound

Participants

Reaction Steps

To a solution of 4-bromophenol (4.94 g., 28.55 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen atmosphere was added dropwise a solution of potassium t-butoxide (1 M solution in THF, 28.6 mL, 28.6 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes, then a solution of Example 17A (2 g, 11.4 mmol) in anhydrous tetrahydrofuran (20 mL) was added and refluxed for 8 hours. The reaction mixture was allowed to cool to 25° C., methyl thioglycolate (1.23 mL, 13.7 mmol) was added and refluxed for 15 minutes. The cooled reaction mixture was diluted with ethyl acetate (300 mL) and partitioned with an ice cold solution of 1 N NaOH (3×75 mL). The organic layer was washed with brine (3×100 mL), dried (MgSO4) and solvents were removed under reduced pressure to obtain the crude product (4.2 g). This was purified by flash chromatography on silica gel eluting with 10% acetone-hexane to obtain the title compound (1.81 g) in 44% yield.

Provenance & Evidence