Bromide ion → 1-(5-Bromopentyl)-3-n-pentylurea

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Reaction Steps

Following the protocol described above, 1-(5-hydroxypentyl)-3-n-pentylurea (1.30 g, 6.02 mmol) was converted into the corresponding bromide (1.45 g, 87%), obtained as a colorless oil. TLC: EtOAc/hexanes (2:3), Rf˜0.40; 1H NMR (300 MHz) δ 4.44 (br s, —NH, 2H), 3.40 (t, J=6.7 Hz, 2H), 3.10-3.20 (m, 4H), 1.82-1.92 (m, 2H), 1.40-1.58 (m, 6H), 1.24-1.38 (m, 4H), 0.89 (t, J=7.3 Hz, 3H); 13C NMR (100 MHz) δ 159.46, 40.02, 33.88, 33.02, 30.29, 29.92, 29.36, 25.83, 22.12, 14.02. HRMS calcd for C11H24BrN2O [M+1]+ 279.1072. found 279.1073.

Provenance & Evidence