Cesium carbonate → (E)-2-(3,3-diethoxyprop-1-enyl)-1-fluoro-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 3,3-diethoxy-1-propenylboronic acid pinacol ester (0.154 mL, 0.600 mmol, Frontier Scientific), 2-bromo-1-fluoro-3-nitrobenzene (110 mg, 0.500 mmol, Aldrich), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (40.8 mg, 0.050 mmol, Strem) and cesium carbonate (326 mg, 1.00 mmol, Aldrich) in dioxane (3 mL) and water (0.5 mL). The reaction mixture was stirred and heated in an Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material. The crude product was purified by silica gel chromatography eluting with 10% EtOAc/hexanes to give (E)-2-(3,3-diethoxyprop-1-enyl)-1-fluoro-3-nitrobenzene (82 mg, 0.305 mmol, 60.9% yield). 1H NMR (300 MHz, CDCl3) δ 1.26 (t, J=7.02 Hz, 6H) 3.45-3.81 (m, 4H) 5.09 (d, J=4.09 Hz, 1H) 6.16-6.37 (m, 1H) 6.76 (d, J=17.25 Hz, 1H) 7.29-7.53 (m, 2H) 7.57-7.75 (m, 1H). m/z (ESI, +ve ion) 270 (M+H)+.

Provenance & Evidence