Water → Bromoethynyl triisopropylsilane

HRID 623671

Reaction equation

HRID 623671 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]([Si:12]([C:19]#[CH:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10].CCCCC.O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:8][C:20]#[C:19][Si:12]([CH:13]([CH3:14])[CH3:15])([CH:9]([CH3:11])[CH3:10])[CH:16]([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 8003PentaneHCID 67184N-bromobutanimideHCID 2734682(Triisopropylsilyl)acetylene

Product 1

HCID 11196280Bromoethynyl triisopropylsilane

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

NBS (2.14 g, 12 mmol) and AgNO3 (170 mg, 1 mmol) were added to a solution of triisopropylsilylacetylene (2.24 ml, 10 mmol) in acetone (15 ml). The solution was stirred for 2 hours at RT. Pentane (20 ml) and H2O (20 ml) were added and the solution was stirred for 30 minutes. The organic phase was extracted with pentane (3×20 ml) and dried over Na2SO4. The solvent was removed under reduced pressure at RT and the residue was used in the next reaction without any purification.

Workup

  1. stirringthe solution was stirred for 30 minutes
  2. extractionThe organic phase was extracted with pentane (3×20 ml)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure at RT
  5. customthe residue was used in the next reaction without any purification

Sources & evidence

ORD record
ord-087145f8e7ff4a7eb7f1c6f990882090
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Linked notes

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