反应详情

温度

-78 °C

2-(2-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (JWH-250) 4 (3 g, 8.94 mmol) was dissolved in anhydrous dichloromethane (40 ml) and cooled at −78° C. A solution of 1NBBr3 (9.83 ml, 9.83 mmol) was added dropwise and once the addition was complete the reaction mixture was allowed to warm up to room temperature and was stirred at room temperature overnight. The reaction mixture was poured into a solution of 2NHCl (100 ml) and stirred for 30 min, then extracted three times with dichloromethane (3×150 ml) and the combined organic fractions dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 0%-20% ethyl acetate in hexane) to give 840 mg (29%) of 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (O-desmethyl JWH-250) 5 as a solid.

1. additionA solution of 1NBBr3 (9.83 ml, 9.83 mmol) was added dropwise
2. additiononce the addition
3. temperatureto warm up to room temperature
4. additionThe reaction mixture was poured into a solution of 2NHCl (100 ml)
5. stirringstirred for 30 min
6. extractionextracted three times with dichloromethane (3×150 ml)
7. dry with materialthe combined organic fractions dried over sodium sulphate
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 0%-20% ethyl acetate in hexane)