Sulfuric Acid → (E)-3-(4-bromo-2-fluoro-6-nitrophenyl)acrylaldehyde

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Reaction Steps

A mixture of (E)-2-(3,3-diethoxyprop-1-enyl)-1-fluoro-3-nitrobenzene (63.5 mg, 0.22 mmol), 1,3-dibromo-5,5-dimethylhydantoin (63.5 mg, 0.222 mmol, Aldrich) and sulfuric acid, 95% (0.5 mL, 7.14 mmol) was stirred at room temperature for 4 h. Ice (5 g) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with saturated NaCl (6 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow oil. The crude product was purified by silica gel chromatography eluting with 20% EtOAc/hexanes to give (E)-3-(4-bromo-2-fluoro-6-nitrophenyl)acrylaldehyde (46 mg, 0.168 mmol, 39.3% yield). 1H NMR (300 MHz, CDCl3) δ 7.47-7.58 (m, 1H) 7.58-7.71 (m, 1H) 8.10 (d, J=8.33 Hz, 1H) 8.15 (s, 1H) 9.50 (s, 1H). m/z (ESI, +ve ion) 273 (M+H)+.

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