Tetraethoxysilane → HCID 13033313, compound

HRID 1349925Notes

Reaction equation

HRID 1349925 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.[CH2:10]([O:12][Si:13](OCC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH3:11]>C(OCC)C>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([Si:13]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[O:12][CH2:10][CH3:11])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 6517TetraethoxysilaneHCID 78041,4-DibromobenzeneHCID 5462224Magnesium

Product 1

HCID 13033313HCID 13033313, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Freshly activated magnesium (8.5 g, 0.35 mol) was slowly added over a period of four hours to a solution of 1,4-dibromobenzene (80 g, 0.34 mol) in 200 mL of diethylether, keeping the temperature below 30° C. The reaction mixture was stirred for 8 h and then slowly added to a mixture of tetraethoxysilane (100 mL, 0.44 mol) in Et2O (50 mL). The mixture was stirred for 12 h, and unreacted tetraethoxysilane and diethylether were removed in vacuum. The remaining liquid was fractionally distilled through a Vigreux column under reduced pressure to provide 4-bromophenyltriethoxysilane as a clear oil (37 g, 37%, bp 80–90° C. at 250 μHg). 1HNMR(400 MHz, CDCl3): δ 7.56 (4H, dd), 3.89 (6H, q), 1.27 (9H, t). 13CNMR (100 MHz, CDCl3): δ 136.4, 131.1, 58.8, 18.2. GC-MS: 318 (M+).

Workup

  1. customthe temperature below 30° C
  2. stirringThe mixture was stirred for 12 h
  3. customunreacted tetraethoxysilane and diethylether were removed in vacuum
  4. distillationThe remaining liquid was fractionally distilled through a Vigreux column under reduced pressure

Sources & evidence

ORD record
ord-c244a9fde0d14fa98163402182b88532
Source dataset
uspto-grants-2007_05
Patent number
US07214475B2

Reaction notes

Loading…