Benzene → 5-(2-Methoxyphenyl)-2-furancarboxaldehyde

Participants

Reaction Steps

To a benzene (10 mL) solution of 5-bromo-2-furaldehyde 7 (350 mg, 2.0 mmol) and 2-methoxyphenylboronic acid 8 (304 mg, 2.0 mmol) was added tetrakis(triphenylphosphine)-palladium(0) (69.4 mg, 0.06 mmol) and sat. aq. K2CO3 solution (4.94 ml, 4.0 mmol) at 21° C. under an argon atmosphere. The reaction mixture was refluxed for 2 h. The mixture was then cooled and diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×20 mL), then dried with brine and MgSO4 and concentrated in vacuo. Flash column chromatography on silica gel (hexane:ethyl acetate=20:1) of the residue afforded 5-(2-methoxyphenyl)-2-furaldehyde 9 in 65% yield (265 mg, yellow oil). 1H NMR (400 MHz, CDCl3): δ 9.65 (s, 1H), 8.05 (dd, J=8.0, 2.0 Hz, 1H), 7.39-7.35 (m, 1H), 7.33 (d, J=3.6 Hz, 1H), 7.14 (d, J=4.0 Hz, 1H), 7.07 (dt, J=7.2, 0.8 Hz, 1H), 7.00 (bd, J=8.0 Hz, 1H), 3.97 (s, 3H).

Provenance & Evidence