反应详情

A solution of 2-bromo-6-fluorobenzaldehyde (3.3 g, 16 mmol) and (trimethylsilyl)acetylene (4.5 mL, 32 mmol) in anhydrous N,N-dimethylformamide (60 mL) was treated with triethylamine (3.5 mL, 25 mmol), copper(I) iodide (0.3 g, 1.6 mmol), and Pd(PPh3)2Cl2 (0.6 g, 0.80 mmol) under argon atmosphere. The mixture was stirred at RT for 2.5 h. The mixture was poured into water (150 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with water (2×75 mL), brine (100 mL) then dried over anhydrous sodium sulfate and evaporated to yield the crude product which was purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 2-fluoro-6-(2-(trimethylsilyl)ethynyl)benzaldehyde 2-bromo-6-fluorobenzaldehyde as a brown oil. MS (ESI, pos. ion) m/z: 221 (M+1).

1. extractionextracted with ethyl acetate (2×150 mL)
2. washThe combined organic layers were washed with water (2×75 mL), brine (100 mL)
3. dry with materialthen dried over anhydrous sodium sulfate
4. customevaporated
5. customto yield the crude product which
6. customwas purified by silica gel chromatography (20-30% EtOAc in hexanes)