Sulfuric Acid → 1-Chloro-4-(1-trimethylsilylhexyl)benzene

HRID 248567

Reaktionsgleichung

Reaktionsgleichung von HRID 248567
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl.S(=O)(=O)(O)O>BrCCCCCCC1C=CC(Cl)=CC=1.O1CCCC1.COC(C)(C)C.[Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]([Si:17]([CH3:20])([CH3:19])[CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH3:3])=[CH:10][CH:11]=1

Komponenten

9

Edukt 4

HCID 1118Sulfuric AcidHCID 6397ChlorotrimethylsilaneHCID 5806791-(6-Bromohexyl)-4-chlorobenzeneHCID 5462224Magnesium

Produkt 1

HCID 197638591-Chloro-4-(1-trimethylsilylhexyl)benzeneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 193501Copper;dilithium;tetrachlorideKatalysatorHCID 5806791-(6-Bromohexyl)-4-chlorobenzeneKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×HCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Approximately 2 g (82 mMol) of magnesium in a flask were moistened with tetrahydrofuran. A Grignard reaction was initiated using 5 drops of 1-(6-bromohexyl)-4-chlorobenzene. The remainder of a total of 17 g of the halogen compound (61 mMol), dissolved in 50 ml of tetrahydrofuran, was added dropwise at 50° to 60° C. When the addition was complete, the mixture was kept at this temperature for an additional 2.5 hours, and a solution of 12 g (110 mMol) of trimethylchlorosilane and a catalytic amount of dilithium tetrachlorocuprate in 40 ml of tetrahydrofuran was then added dropwise at 20° to 40° C. The mixture was stirred at 60° C. for 1 hour, then allowed to stand overnight and diluted with 200 ml of tert-butyl methyl ether. The mixture was then acidified using 2N sulfuric acid, the phases were separated, and the organic phase was washed and dried. The evaporated residue was fractionated. About 6.4 g of 1-chloro-4-(1-trimethylsilylhexyl)benzene (38.6 percent yield) were obtained at a pressure of 0.2 hPa and at 88° to 90° C.

Aufarbeitung

  1. customA Grignard reaction
  2. additionwas added dropwise at 50° to 60° C
  3. additionWhen the addition
  4. waitto stand overnight
  5. customthe phases were separated
  6. washthe organic phase was washed
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-199d6f6eb60e456080d3e5aa1cc42175
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210247

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