Benzyl Bromide → 4-(3-Benzyloxycarbonyl-propoxy)-phenylboronic acid

Participants

Reaction Steps

A solution of 1A (200 mg, 0.89 mmol), potassium bicarbonate (313 mg, 3.1 mmol), and benzyl bromide (0.163 mL, 1.4 mmol) in DMF (2 mL) was heated at 60° C. for 8 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and hydrochloric acid (1 N). The aqueous layer was extracted with EtOAc (2×) and then the combined organics were washed with water (3×) and brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (30 to 100% EtOAc in hexane) to afford 1B (86 mg, 28%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 2.08 (m, 2H), 2.56 (t, J=7.0 Hz, 2H), 4.00 (m, 2H), 5.12 (s, 2H), 6.84 (2×d, 2H), 7.32 (m, 5H), 7.7-7.5 (2×d, 2H).

Provenance & Evidence