Tributyltin Chloride → TRIBUTYL(4-METHOXYPHENYL)STANNANE

Temperature

60 °C

To tributyltin chloride (652 mg, 2.00 mmol, 1.00 equiv) in THF (2 mL) at 23° C. was added 4-methoxyphenylmagnesium bromide (0.50 M in THF, 8.0 mL, 4.0 mmol, 2.0 equiv). After stirring for 1.0 hr at 60° C., the reaction mixture was cooled to 0° C. and quenched with saturated aqueous NH4Cl (10 mL), and Et2O (10 mL) was added. The phases were separated and the aqueous phase was extracted with Et2O (2×10 mL). The combined organic phases were washed with brine (10 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by fractional distillation to afford 637 mg of the title compound as a colorless oil (80% yield).

1. temperaturethe reaction mixture was cooled to 0° C.
2. customquenched with saturated aqueous NH4Cl (10 mL), and Et2O (10 mL)
3. additionwas added
4. customThe phases were separated
5. extractionthe aqueous phase was extracted with Et2O (2×10 mL)
6. washThe combined organic phases were washed with brine (10 mL)
7. dry with materialdried (Na2SO4)
8. concentrationThe filtrate was concentrated in vacuo
9. distillationthe residue was purified by fractional distillation

ORD record

ord-35f2ab8166e645d58d780cb2a677545c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024093B2