Sodium Iodide → 5-(4-Bromophenyl)-3,4-dihydro-2h-pyrrole

Temperature

55 °C

A mixture of 4′-bromo-4-chlorobutyrophenone (20.0 g, 76.5 mmol), sodium azide (7.46 g, 115 mmol) and sodium iodide (344 mg, 2.29 mmol) is stirred overnight at 55° C. The reaction mixture is poured on water and extracted with DCM. The organic phases are dried over MgSO4 and concentrated in vacuo. The residue is dissolved in 150 mL cyclohexane, triphenylphosphine (20.1 g, 76.5 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is filtered and the solids are washed with cold diethyl ether. The filtrate is concentrated in vacuo, water is added and the mixture is extracted with DCM. The combined organic phases are washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue is treated with a mixture diethyl ether/cyclohexane (1/1, v/v), filtered and the filtrate is concentrated in vacuo. Yield: 15.6 g.

1. additionThe reaction mixture is poured on water
2. extractionextracted with DCM
3. dry with materialThe organic phases are dried over MgSO4
4. concentrationconcentrated in vacuo
5. dissolutionThe residue is dissolved in 150 mL cyclohexane
6. stirringthe reaction mixture is stirred overnight at RT
7. filtrationThe reaction mixture is filtered
8. washthe solids are washed with cold diethyl ether
9. concentrationThe filtrate is concentrated in vacuo, water
10. additionis added
11. extractionthe mixture is extracted with DCM
12. washThe combined organic phases are washed with water and brine
13. dry with materialdried over MgSO4
14. concentrationconcentrated in vacuo
15. additionThe residue is treated with a mixture diethyl ether/cyclohexane (1/1
16. filtrationv/v), filtered
17. concentrationthe filtrate is concentrated in vacuo

ORD record

ord-d3197924e2da4134ac011d1e80f5bbf4

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304556B2