Hydrochloric Acid → 2,4-Dibromobenzonitrile

温度

45 °C

Copper cyanide (2.32 g, 25.9 mmol) is added to stirred anhydrous dimethylsulfoxide (50 mL) at 60° C. to form a clear solution, followed by the addition of tert-butylnitrite (7.1 mL, 59.7 mmol) all at once. A solution of 2,4-dibromoaniline 21 (5.0 g, 19.9 mmol) in anhydrous dimethylsulfoxide (30 mL) is added dropwise, via cannula, to the mixture. After the addition is complete, the reaction mixture is allowed to stir for 1 hr. After being cooled to 45° C., the mixture is slowly treated with 5N hydrochloric acid (50 mL). Five minutes later, the reaction mixture is cooled to ambient temperature before being extracted with ethyl acetate/hexane (1:1; 2×300 mL). The combined organic layers are washed with water (100 mL) and brine (100 mL), dried, concentrated in vacuo, and then chromatographed on silica (0–5% ethyl acetate in hexane) to give the title compound (1.61 g, 31% yield). FD(+)MS m/z 259, (M+) consistent with 2 Br.

1. customto form a clear solution
2. additionAfter the addition
3. temperatureFive minutes later, the reaction mixture is cooled to ambient temperature
4. extractionbefore being extracted with ethyl acetate/hexane (1:1; 2×300 mL)
5. washThe combined organic layers are washed with water (100 mL) and brine (100 mL)
6. customdried
7. concentrationconcentrated in vacuo
8. customchromatographed on silica (0–5% ethyl acetate in hexane)

ORDレコード

ord-55e97c7bfb3c4a3b8e73d36580db020d

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07084170B2