Tributyltin Chloride → Benzonitrile, 4-(tributylstannyl)-

Temperature

-40 °C

To 4-iodobenzonitrile (2.29 g, 10.0 mmol, 1.00 equiv) in THF (30 mL) at −40° C. was added iPrMgCl (2.0 M in Et2O, 5.50 mL, 11 mmol, 1.1 equiv). The reaction mixture was stirred for 1.0 hr at −40° C. before the addition of nBu3SnCl (3.91 g, 12.0 mmol, 1.20 equiv). After stirring for 1.0 hr at −40° C., the reaction mixture was warmed to 23° C. and quenched with saturated aqueous NH4Cl (30 mL), and Et2O (20 mL) was added. The phases were separated and the aqueous phase was extracted with Et2O (2×20 mL). The combined organic phases were washed with brine (50 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with hexanes to afford 3.14 g of the title compound as a colorless oil (80% yield).

1. temperaturethe reaction mixture was warmed to 23° C.
2. customquenched with saturated aqueous NH4Cl (30 mL), and Et2O (20 mL)
3. additionwas added
4. customThe phases were separated
5. extractionthe aqueous phase was extracted with Et2O (2×20 mL)
6. washThe combined organic phases were washed with brine (50 mL)
7. dry with materialdried (Na2SO4)
8. concentrationThe filtrate was concentrated in vacuo
9. customthe residue was purified by chromatography on silica gel eluting with hexanes

ORD record

ord-2d32e2e6610445cf90a708554c9f0661

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024093B2