4-Toluenesulfonyl chloride → HCID 21925012, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Bromophenyl)ethyl alcohol (2.01 g, 10 mmol) was dissolved in DCM (50 mL) and cooled to 0° C. After addition of triethylamine (1.52 g, 15 mmol) and tosyl chloride (1.91 g, 10 mmol) the reaction was stirred at room temperature overnight. TLC indicated complete conversion of the starting material. DCM was evaporated, the mixture was diluted with EtOAc and washed subsequently with aqueous hydrochloric acid (1 N), water, saturated sodium hydrogen carbonate and brine. Drying and evaporation afforded an oil, which was dissolved in anhydrous DMF (10 mL). Sodium azide (1.3 g, 20 mmol) was added and the mixture heated to 40° C. for 16 h. After cooling to room temperature, EtOAc was added and the solution was washed with water (4×) and brine. The resulting oil was filtered over (100 g) with the aid of PE/EtOAc (10:1) to obtain 2-(3-bromophenyl)ethyl azide (1.63 g, 72% ) as a colorless oil. 1H-NMR (CDCl3) δ 7.39 (m, 2 H), 7.16–7.22 (m, 2 H), 4.51 (bs, 1 H), 3.50 (d, J=6.6 Hz, 2 H), 2.83 (t, J=6.6 Hz, 2 H).

Provenance & Evidence