Iodine → Diisopropyl(2,2-dimethylpropyl)silane

HRID 1169565Notes

Reaction equation

HRID 1169565 reaction equation
[Mg].II.Br[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].C([SiH:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])CCC>C1COCC1>[CH:15]([SiH:14]([CH:18]([CH3:20])[CH3:19])[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 807IodineHCID 124151-Bromo-2,2-dimethylpropaneHCID 5462224MagnesiumHCID 123687559n-Butyldiisopropylsilane

Product 1

HCID 123529220Diisopropyl(2,2-dimethylpropyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (2.43 g, 100 mmol) and iodine (catalytic amount) were added to THF (100 mL), and 1-bromo-2,2-dimethylpropane (10.7 mL, 100 mmol) was added dropwise thereto for 20 minutes, followed by stirring at room temperature for 1 hour. After termination of exothermic reaction, the resultant mixture was further stirred at 50° C. for 5 hours, whereby 2,2-dimethylpropylmagnesium bromide THF solution was prepared. The procedure of synthesizing Compound 47a was repeated, except that the thus-prepared mixture was employed, whereby the Compound 51a was obtained as a colorless liquid (boiling point; 40 mmHg, 120.0 to 122.5° C. fraction, 7.65 g, 45%).

Workup

  1. additionwas added dropwise
  2. customAfter termination of exothermic reaction

Sources & evidence

ORD record
ord-a32c7b354f9e434caaba94e683626155
Source dataset
uspto-grants-2010_11
Patent number
US07825103B2

Reaction notes

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