2-(4-Bromophenyl)ethanol → 4-Bromophenethyl 3-cyanophenylcarbamate

Participants

Reaction Steps

Titanium tetra-tert-butoxide (0.080 mL, 0.21 mmol) was added dropwise to a solution of 3-cyanophenylisocyanate (228 mg, 1.58 mmol) and 2-(4-bromophenyl)ethanol (606 mg, 3.01 mmol) in toluene (10 mL). A precipitate formed immediately and the reaction was stirred for 2 h at rt. The reaction was quenched with saturated ammonium chloride solution and extracted with DCM (3×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo. The residual solid was triturated with DCM hexane to give 11A (543 mg, 100%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.95 (t, J=6.81 Hz, 2 H), 4.38 (t, J=6.81 Hz, 2 H), 6.68 (s, 1 H), 7.11 (d, J=8.35 Hz, 2 H), 7.31-7.35 (m, 1 H), 7.38 (t, J=7.91 Hz, 1 H), 7.44 (d, J=8.35 Hz, 2 H), 7.52 (d, J=7.03 Hz, 1 H), 7.76 (s, 1 H).

Provenance & Evidence