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3,7-Dimethyloctyl trichlorosilane → Bis(3,7-dimethyloctyl)dichlorosilane

HRID 1772574
Notes
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Reaction equation

HRID 1772574 reaction equation
[CH3:1][CH:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][CH2:4][Si:5]([Cl:8])([Cl:7])Cl.[CH3:15][CH:16]([CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:18][Mg]Br>O1CCCC1>[CH3:15][CH:16]([CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:18][Si:5]([CH2:4][CH2:3][CH:2]([CH3:1])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])([Cl:7])[Cl:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1240151143,7-Dimethyloctyl trichlorosilaneHCID 178443368HCID 178443368, compound

Product 1

HCID 78062573Bis(3,7-dimethyloctyl)dichlorosilaneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Tetrahydrofuran (50 mL) and 3,7-dimethyloctyl trichlorosilane (11.27 g, 40.9 mmol) were placed in a 200 mL four-necked flask in a nitrogen atmosphere, and cooled to −20° C. 3,7-dimethyloctyl magnesium bromide (Sigma-Aldrich Co. LLC., 1.0 M, 42.9 ml) was added dropwise, and the mixture was agitated for 1 hour at 10° C. or less. The temperature was raised gradually to room temperature over the course of about 1 hour, and the mixture was left standing overnight. The precipitated salt was filtered out, the tetrahydrofuran was removed by concentration under reduced pressure, and the mixture was distilled under reduced pressure to obtain the target bis(3,7-dimethyloctyl)dichlorosilane (Compound E27) (150-152° C./0.6 Torr, 11.3 g, yield 73%).

Workup

  1. temperatureThe temperature was raised gradually to room temperature over the course of about 1 hour
  2. waitthe mixture was left
  3. waitstanding overnight
  4. filtrationThe precipitated salt was filtered out
  5. customthe tetrahydrofuran was removed by concentration under reduced pressure
  6. distillationthe mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-555af8b2282744d582d33e77e104411b
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249257B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes