Triethylamine → Triphenyl-(2,4,6-trichlorophenylethynyl)silane

HRID 735085Notes

Reaction equation

HRID 735085 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[Cl:10].[C:11]1([Si:17]([C:30]#[CH:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCOCC1.[Cu]I>[C:24]1([Si:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:30]#[C:31][C:2]2[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=2[Cl:10])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1405262-Bromo-1,3,5-trichlorobenzeneHCID 642601(Triphenylsilyl)acetylene

Product 1

HCID 86060684Triphenyl-(2,4,6-trichlorophenylethynyl)silane

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

In an argon atmosphere, 9 g (34.6 mmol) of 1-bromo-2,4,6-trichlorobenzene, 9.8 g (34.45 mmol) of triphenylsilylacetylene, and 15 mL of triethylamine are dissolved in 100 mL of absolute dioxane and at 90° C. combined with 0.2 g (1.04 mmol) of copper (I) iodide and 1.2 g (1.04 mmol) of tetrakistriphenylphosphine palladium and stirred for 20 hours. The reaction mixture is filtered through CELITE® filter aid and the filtrate is evaporated down. The residue is taken up in ethyl acetate and extracted with water. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether/toluene (5:1)). The product is recrystallized from petroleum ether and dried in the vacuum drying chamber at 70° C. Yield: 6.9 g (43% of theory); melting point: 115° C.-120° C.; C26H17Cl3Si (M=463.87); calc.: molecular ion peak (M+H)+: 463/465/467/469; found: molecular ion peak (M+H)+: 463/465/467/469; Rf value: 0.6 (silica gel, petroleum ether/toluene (4:1)).

Workup

  1. filtrationThe reaction mixture is filtered through CELITE®
  2. filtrationfilter aid
  3. customthe filtrate is evaporated down
  4. extractionextracted with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customThe purification
  7. customThe product is recrystallized from petroleum ether
  8. customdried in the vacuum
  9. customdrying chamber at 70° C

Sources & evidence

ORD record
ord-32f5de46a19b44a3a11dfaffc5a41dc8
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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