Sulfuric Acid → HCID 52448820, compound

Participants

Reaction Steps

To a solution of (E)-3-(3-bromophenyl)acrylic acid (7.5 g, 32.4 mmol) in propan-2-ol (50 mL, 832 mmol) was added dropwise H2SO4 (0.431 mL, 8.09 mmol). The reaction was heated to reflux for 18 h then it was concentrated in vacuo providing a brown liquid which was redissolved in 50 mL ethylacetate. 1N NaOH was added dropwise until the aqueous mixture reached pH10. The organic layer was collected and washed with aqueous sodium bicarbonate (sat), brine, dried over magnesium sulfate, filtered and concentrated providing (E)-isopropyl 3-(3-bromophenyl)acrylate (8.4202 g, 29.7 mmol, 92% yield) as a yellow liquid. 1H NMR (500 MHz, DMSO) δ 7.98 (s, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.67-7.55 (m, 2H), 7.37 (t, J=7.9 Hz, 1H), 6.70 (d, J=16.0 Hz, 1H), 5.02 (dt, J=12.5, 6.2 Hz, 1H), 1.26 (d, J=6.3 Hz, 6H). Mass spec.: 270.88 (MH)+.

Provenance & Evidence