1-Bromo-2-ethylbenzene → (2-Ethyl-phenyl)-3,3-dimethylbutyl-dimethoxysilane

HRID 2086389Notes

Reaction equation

HRID 2086389 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH3:10].[CH3:11][C:12]([CH3:23])([CH3:22])[CH2:13][CH2:14][Si:15](OC)([O:18][CH3:19])[O:16][CH3:17].[SiH4]>C(O)C.O1CCCC1>[CH2:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[Si:15]([CH2:14][CH2:13][C:12]([CH3:23])([CH3:22])[CH3:11])([O:18][CH3:19])[O:16][CH3:17])[CH3:10]

Participants

7

Reactant 4

HCID 160891-Bromo-2-ethylbenzeneHCID 23953SilaneHCID 5462224MagnesiumHCID 22238663(3,3-Dimethylbutyl)trimethoxysilane

Product 1

HCID 12135720(2-Ethyl-phenyl)-3,3-dimethylbutyl-dimethoxysilaneYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of dry nitrogen a magnetically stirred suspension of anhydrous tetrahydrofuran (Aldrich, 300 mL) and magnesium turnings (Aldrich, 1.2 g, 49 mmol) was treated dropwise at room temperature with 1-bromo-2-ethylbenzene (Aldrich, 6.1 mL, 44 mmol). After 10 minutes the reaction mixture began to reflux mildly. After the addition was complete the reaction mixture was heated to reflux overnight (18 h). A separate flask was flushed with dry nitrogen and then charged with anhydrous tetrahydrofuran (Aldrich, 100 mL) and 3,3-dimethylbutyl-trimethoxysilane (Huls, 11.4 mL, 49 mmol). The Grignard solution was cooled to room temperature and then added to the silane solution at room temperature via stainless steel cannula. The reaction mixture stirred at room temperature overnight (18 h). Ethyl alcohol (Aldrich, 5 mL) was added to quench any remaining Grignard. The reaction mixture was concentrated on a rotary evaporator and distilled in vacuum to give 3.7 g (30%) of the title compound as a colorless oil (b.p. 107-108° C. at 0.5 mm Hg, 99% GC-purity): C16H28O2Si (Mw=280).

Workup

  1. temperatureto reflux mildly
  2. additionAfter the addition
  3. temperaturewas heated
  4. temperatureto reflux overnight (18 h)
  5. customA separate flask was flushed with dry nitrogen
  6. customto quench any remaining Grignard
  7. concentrationThe reaction mixture was concentrated on a rotary evaporator
  8. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-7233c7afa5e847dd9e05fd620f6b3922
Source dataset
uspto-grants-2004_04
Patent number
US06723865B2

Reaction notes

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