Carbon tetrabromide → (2-(2-Bromoethoxy)ethoxy)(tert-butyl)dimethylsilane

HRID 651505

Reaction equation

HRID 651505 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[CH3:6][C:7]([Si:10]([CH3:19])([CH3:18])[O:11][CH2:12][CH2:13][O:14][CH2:15]CO)([CH3:9])[CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:5][CH2:1][CH2:15][O:14][CH2:13][CH2:12][O:11][Si:10]([C:7]([CH3:9])([CH3:8])[CH3:6])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanol

Product 1

HCID 18185637(2-(2-Bromoethoxy)ethoxy)(tert-butyl)dimethylsilaneYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18.2 g of carbon tetrabromide is added over 15 minutes at −15°/−20° C. to a mixture containing 11.2 g of the product of Stage A and 14.4 g of triphenylphosphine in 100 cm3 of methylene chloride. Agitation is carried out for 1 hour 15 minutes at −15° C., the solvent is evaporated off, followed by taking up in pentane, agitating at ambient temperature, separating, washing with pentane and drying at 50° C. under reduced pressure. 10.1 g of expected product is obtained.

Workup

  1. customthe solvent is evaporated off
  2. customseparating
  3. washwashing with pentane
  4. customdrying at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-bcb4d5119b454cbbad52625271afd587
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Linked notes

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