Methyl Acrylate → Methyl 2-((4-bromophenyl)(hydroxy)methyl)acrylate

Participants

Reaction Steps

A solution of 2.46 g (13.3 mmol) of 4-bromobenzaldehyde, 1.0 mL (11.1 mmol) of methyl acrylate and 125 mg (1.11 mmol) of 1,4-diazobicyclo[2.2.2]octane in 5 mL MeOH was stirred at ambient temperature for 46 hr. The solvent was evaporated and the residue taken up in EtOAc. The organics were washed with 0.5 N HCl (aq), then with brine, and concentrated. The residue was purified by silica gel chromatography (120 g of silica gel eluting with 0-30% EtOAc in hexanes over 45 minutes) to give 1.42 g (40%) of methyl 2-[(4-bromophenyl)(hydroxy)methyl]-2-propenoate as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.47 (d, J=2 Hz, 2H), 7.27 (d, J=2 Hz, 2H), 6.33 (s, 1H), 5.82 (s, 1H), 5.51 (d, J=5 Hz, 1H), 3.72 (s, 3H), 3.07 (d, J=5 Hz, 1H). ESI-LCMS m/z 293 (M+Na)+.

Provenance & Evidence