Example 64: Synthesis of tert-butyl 2-bromobenzoate
Step A. To a solution of 2-bromobenzoyl chloride (2.0 g, 9.11 mmol) in anhydrous ethyl ether (40 mL) was added sequentially tert-butanol (0.96 mL, 10.02 mmol) and 4-(dimethylamino)pyridine (111 mg, 0.91 mmol). The reaction mixture was stirred at room temperature for 48 hours under nitrogen protection. After completion of the reaction, the resulting white suspension was extracted by partitioning with ethyl acetate (100 mL) and 1 M hydrochloric acid (100 mL). The organic phase was separated and washed sequentially with 1 M hydrochloric acid (100 mL), 2 M sodium hydroxide (2 x 100 mL), water (100 mL) and saturated saline (100 mL). The organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give a yellow oil. Purification by fast column chromatography with ethyl acetate/hexane as eluent gave tert-butyl 2-bromobenzoate (1.22 g, 52% yield) as a colorless oil.
