Bromoacetonitrile → Tosylacetonitrile

HRID 2061642Notes

Reaction equation

HRID 2061642 reaction equation
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

Participants

6

Reactant 2

HCID 11534BromoacetonitrileHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 79776TosylacetonitrileYield 54%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d3bb4f395a0b4bfc9a3498c1b9d97497
Source dataset
uspto-grants-2012_10
Patent number
US08283378B2

Reaction notes

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