Diethyl Ether → Stannane, (4-chlorophenyl)trimethyl-

To a 1M solution of trimethyltin chloride in THF (92 ml, 92 mmol) was slowly added a 1M solution of 4-chlorophenylmagnesium bromide in Et2O (92 ml, 92 mmol) over a 40 min period at −10° C. so that the temperature never exceed 0° C. After the addition, the cooling bath was removed and the resulting suspension was stirred at RT for 1 h. A saturated aqueous solution of NH4Cl (14 ml) was added followed by water until complete dissolution of the precipitate. The mixture was transferred into a separating funnel and extracted with Et2O (3×). The combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; isocratic elution with cyclohexane) to yield the title compound (24.47 g, 89 mmol, 97%) as a colorless oil. TLC: RF=0.76 (cyclohexane/AcOEt 95:5); HPLC: AtRet=3.25 min; 1H NMR (400 MHz, CDCl3): 0.31 (s, 9H) 7.32-7.36 (m, 2H) 7.41-7.45 (m, 2H).

1. additionAfter the addition
2. customthe cooling bath was removed
3. additionA saturated aqueous solution of NH4Cl (14 ml) was added
4. dissolutionfollowed by water until complete dissolution of the precipitate
5. customThe mixture was transferred into a separating funnel
6. extractionextracted with Et2O (3×)
7. dry with materialThe combined organic fractions were dried over Na2SO4
8. filtrationfiltered
9. customevaporated to dryness
10. customThe resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; isocratic elution with cyclohexane)

ORD record

ord-50a7aa08e4424521a6a094c339b5a144

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051279B2