Dichlorodimethylsilane → HCID 58418820, compound

HRID 557499Notes

Reaction equation

HRID 557499 reaction equation
[Mg].BrCCBr.[C:6]([C:10]1[CH:11]=[C:12]2[C:16](=[C:17](Br)[CH:18]=1)[CH2:15][C:14]([CH3:20])=[CH:13]2)([CH3:9])([CH3:8])[CH3:7].[Cl:21][Si:22](Cl)([CH3:24])[CH3:23]>C1COCC1>[C:6]([C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([Si:22]([Cl:21])([CH3:24])[CH3:23])[CH:18]=1)[CH2:15][C:14]([CH3:20])=[CH:13]2)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 58418764HCID 58418764, compound

Product 1

HCID 58418820HCID 58418820, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 6.68 g (0.278 mol) of magnesium turnings in 200 mL of dry THF 5.26 g (0.028 mol) of 1,2-dibromoethane was added dropwise for 30 minutes. This mixture was stirred for additional 30 minutes, and then a solution of 66.3 g (0.250 mol) of 5-tert-butyl-2-methyl-7-bromo-1H-indene in 900 mL of THF was added dropwise by vigorous stirring in such rate that the mixture is refluxed. Then, this mixture was additionally refluxed for 30 minutes. Further on, to a solution of 113 g (0.875 mol) of dichlorodimethylsilane in 100 mL of THF the above-obtained solution of the Grignard reagent was added dropwise by vigorous stirring at room temperature using a water bath to cool the reaction mixture. The resulting mixture was additionally stirred for 12 hours at ambient temperature, evaporated to dryness, and then 200 mL of dry ether was added. The obtained suspension was stirred for 20 minutes at room temperature and then filtered through glass frit (G3). The precipitate was additionally washed by 2×100 mL of ether. The combined filtrate was evaporated to dryness, and the residue was rectificated in vacuum, b.p. 147° C.-155° C./1 mm Hg. Yield 50.1 g (72%) of the title product. 1H NMR (CD2Cl2): δ 7.46 (s, 1H, 6-H), 7.43 (s, 1H, 4-H), 6.55 (s, 1H, 3-H), 3.47 (s, 2H, 1,1′-H), 2.22 (s, 3H, 2-Me), 1.41 (s, 9H, tBu), 0.82 (s, 6H, SiMe2). Anal. Calc. for C16H23ClSi: C, 68.91; H, 8.31%. Found: C, 69.13; H, 8.58%.

Workup

  1. stirringby vigorous stirring in such rate that the mixture
  2. temperatureis refluxed
  3. temperatureThen, this mixture was additionally refluxed for 30 minutes
  4. stirringby vigorous stirring at room temperature
  5. temperatureto cool the reaction mixture
  6. stirringThe resulting mixture was additionally stirred for 12 hours at ambient temperature
  7. customevaporated to dryness
  8. addition200 mL of dry ether was added
  9. stirringThe obtained suspension was stirred for 20 minutes at room temperature
  10. filtrationfiltered through glass frit (G3)
  11. washThe precipitate was additionally washed by 2×100 mL of ether
  12. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-757d6424976348f5a3dd06f437cbf058
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

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