4-Toluenesulfonyl chloride → HCID 21925012, compound

Temperature

0 °C

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).

1. customDCM was evaporated
2. additionthe mixture was diluted with EtOAc
3. washwashed subsequently with aqueous hydrochloric acid (1 N), water, saturated sodium hydrogen carbonate and brine
4. customDrying
5. customevaporation
6. customafforded an oil, which
7. temperaturethe mixture heated to 40° C. for 16 h
8. temperatureAfter cooling to room temperature
9. washthe solution was washed with water (4×) and brine
10. filtrationThe resulting oil was filtered over (100 g) with the aid of PE/EtOAc (10:1)

ORD record

ord-f04757a86c494c239856cf9fb7f815e9

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119073B2