Water → Silane, (4-methoxyphenyl)trimethyl-

HRID 525497Notes

Reaction equation

HRID 525497 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Si:10](Cl)([CH3:13])([CH3:12])[CH3:11].[Li]CCCC.O>C1COCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 77304-BromoanisoleHCID 178418339Butyllithium

Product 1

HCID 136689Silane, (4-methoxyphenyl)trimethyl-Yield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromoanisole (9.35 g, 50.0 mmol, 1.0 eq) was dissolved in anhydrous THF (200 mL). Me3SiCl (12.7 mL, 100.0 mmol, 2.0 eq) was added at 0° C. followed by n-BuLi (2.5 M in hexanes, 40 mL, 100.0 mmol, 2.0 eq). The reaction mixture was stirred at room temperature for 1 h. Water (150 mL) was then added, the organic layer was separated and the aqueous layer was extracted with Et2O (150 mL×2). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give (4-methoxyphenyl)trimethylsilane as a light yellow oil (8.1 g, 90% yield). 1H NMR (300 MHz, CDCl3) δ: 7.48 (d, J=11.2 Hz, 2H), 6.95 (d, J=11.2 Hz, 2H), 3.84 (s, 3H), 0.27 (s, 9H).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with Et2O (150 mL×2)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7e5298b57cc422487a8e2aba1a7a143
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

Loading…