Phenethyl bromide → HCID 17135006, compound

Participants

Reaction Steps

3-Hydroxybenzamide (500 mg; 3.6 mM) was dissolved in dry acetonitrile (36 ml), and to this was added potassium carbonate (0.503 g; 3.6mmol) and 2-(bromoethyl)benzene (0.498 ml; 3.6 mmol). The mixture was heated under reflux for two days. The acetonitrile was removed under reduced pressure to yield a white solid. This was dissolved in water and extracted into dichloromethane (3×30 ml). The organics were pooled, dried over magnesium sulphate, filtered and the solvent was removed under reduced pressure to yield a white solid. This was recrystallised from boiling ethyl acetate and petrol (0.459 g; 12.51%). MPt: 132-136° C. 1H: 200 MHz CDCl3 3.05 (2H, t, H8); 4.2 (2H, t, H7); 6.00 (1H, br s, NH); 7.04 (1H, m, H4); 7.27 (9H, m, NH; aromatic). IR cm-1 3300 (NH2); 1666 (CO); 2930 (C=C). M/Z (EI); 241 (M+ ; 18%); 105 (--COHN2 ; 100%). Elemental Analysis: Expected % C15H15O2N C: 74.4, H: 6.20, N: 5.79; Found: % C: 74.7, H:6.2, N:5.8.

Provenance & Evidence