1,4-Dioxane → HCID 59651817, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3-fluorobenzaldehyde (1.00 g, 4.9 mmol) in dioxane (10.0 mL) was added tributyl(1-ethoxyvinyl)stannane (1.7 mL, 5.2 mmol) and Pd(PPh3)2Cl2 (0.069 g, 0.099 mmol). The resulting solution was purged with argon for 2 min and then heated (microwave) in a sealed tube at 130° C. for 30 min. The cooled reaction solution was filtered through a plug of silica gel (eluting with 80 mL EtOAc), and the filtrate was concentrated in vacuo. Chromatographic purification of the residue (ISCO, 40 g, 0-30% EtOAc/Hex) afforded 1-bromo-4-(diethoxymethyl)-2-fluorobenzene as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.98 (s, 1H), 7.81 (t, J=7.5 Hz, 1H), 7.65 (d, J=7.5 Hz, 1H), 7.57 (d, J=11.0 Hz, 1H), 4.90 (d, J=2.0 Hz, 1H), 4.58 (s, 1H), 3.94 (q, J=7.0 Hz, 2H), 1.42 (t, J=6.8 Hz, 3H).

Provenance & Evidence