Dichlorodiphenylsilane → HCID 4351769, compound

HRID 1906292

Reaction equation

HRID 1906292 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl[Si:22](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([Si:22]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 6627Dichlorodiphenylsilane2×HCID 178442890HCID 178442890, compound

Product 1

HCID 4351769HCID 4351769, compoundYield 78%

Procedure

The first portion of the octadecylmagnesium bromide was cooled to 0° and cuprous cyanide (0.12 g 1.34 mmoles) was added with stirring. Then dichlorodiphenylsilane (1.95 ml, 9.27 mmoles) was added. The reaction mixture was stirred at 10° for 140 minutes. Gas chromatographic analysis showed that most of the dichlorodiphenylsilane had disappeared during the first hour of reaction. The mixture was then stirred at room temperature for about 16 hours (i.e. overnight). The reaction mixture was then filtered, quenched with water, and acidified slightly with HCl. After extraction with diethylether, drying (with MgSO4) and removal of solvent, a solid was obtained. Extraction with hot heptane and crystallization provided 4.96 g of dioctadecyldiphenylsilane. The yield was about 78%.

Workup

  1. stirringThe reaction mixture was stirred at 10° for 140 minutes
  2. customhad disappeared during the first hour of reaction
  3. stirringThe mixture was then stirred at room temperature for about 16 hours (i.e. overnight)
  4. filtrationThe reaction mixture was then filtered
  5. customquenched with water
  6. extractionAfter extraction with diethylether
  7. customdrying
  8. custom(with MgSO4) and removal of solvent
  9. customa solid was obtained
  10. extractionExtraction
  11. customwith hot heptane and crystallization

Sources & evidence

ORD record
ord-965c22f5de6a4bfa9e31a0a5b952a12b
Source dataset
uspto-grants-1987_03
Patent number
US04650891

Linked notes

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