Chlorotriethylsilane → [4-(3-Chloro-2-methylpropyl)phenyl](triethyl)silane

HRID 1380030Notes

Reaction equation

HRID 1380030 reaction equation
[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)[CH2:3][Cl:4].[Mg].[CH2:14]([Si:16]([CH2:20][CH3:21])([CH2:18][CH3:19])Cl)[CH3:15]>O1CCCC1>[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Si:16]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:14][CH3:15])=[CH:8][CH:7]=1)[CH2:3][Cl:4]

Participants

5

Reactant 3

HCID 13819ChlorotriethylsilaneHCID 5462224MagnesiumHCID 132921781-Bromo-4-(3-chloro-2-methylpropyl)benzene

Product 1

HCID 13292179[4-(3-Chloro-2-methylpropyl)phenyl](triethyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

a solution of 24.7 parts of 2-methyl-3-(4-bromophenyl)-propyl chloride in 20 parts of tetrahydrofuran (THF) were added dropwise to 2.4 parts of magnesium in 25 parts of THF. The reaction was maintained at from 50° to 52° C., and the mixture was then refluxed for a further 30 minutes. 16.5 parts of triethylchlorosilane were added dropwise at room temperature and the mixture was then refluxed again for 6 hours, cooled and filtered. The solution was concentrated and the residue was distilled to give, at a boiling point of 115°-120° C./0.01 mm Hg, 20.3 parts of 2-methyl-3-(4-triethylsilylphenyl)-propyl chloride of n24 1.5080.

Workup

  1. temperatureThe reaction was maintained at from 50° to 52° C.
  2. temperaturethe mixture was then refluxed for a further 30 minutes
  3. temperaturethe mixture was then refluxed again for 6 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationThe solution was concentrated
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-b369ff4062f7492bb16f56913ee783f1
Source dataset
uspto-grants-1986_04
Patent number
US04579842

Reaction notes

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