Bromoacetonitrile → Tosylacetonitrile

HRID 2061642

Reaktionsgleichung

Reaktionsgleichung von HRID 2061642
Br[CH2:2][C:3]#[N:4].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.CN(C)C=O>[C:6]1([CH3:5])[CH:11]=[CH:10][C:9]([S:12]([CH2:2][C:3]#[N:4])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Komponenten

6

Edukt 2

HCID 11534BromoacetonitrileHCID 2723791Sodium p-toluenesulfinate

Produkt 1

HCID 79776TosylacetonitrileAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3.37 g (28 mmol) of bromoacetonitrile and 640 mg (2.8 mmol) of benzyltriethylammonium chloride are added to a solution of 5 g (28 mmol) of sodium 4-methyl-benzenesulfinate in 50 ml of toluene and 50 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 24 h. The heterogeneous mixture is filtered. The filtrate is evaporated and then purified on silica gel (heptane then heptane/ethyl acetate, 60/40 v/v). The product is triturated in heptane then filtered and dried. 2.95 g of (toluene-4-sulfonyl)-acetonitrile is obtained in the form of a pale yellow powder. (Yield=54%).

Aufarbeitung

  1. filtrationThe heterogeneous mixture is filtered
  2. customThe filtrate is evaporated
  3. custompurified on silica gel (heptane
  4. customThe product is triturated in heptane
  5. filtrationthen filtered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d3bb4f395a0b4bfc9a3498c1b9d97497
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283378B2

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