1,4-Dibromobutane → HCID 1204325, compound

HRID 2061639Notes

Reaction equation

HRID 2061639 reaction equation
[C:1]1([S:7]([CH2:10][C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:1]1([S:7]([C:10]2([C:11]#[N:12])[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 80561,4-DibromobutaneHCID 82077Phenylsulphonylacetonitrile

Product 1

HCID 1204325HCID 1204325, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

629 mg (2.8 mmol) of benzyltriethylammonium chloride is added to 5 g (27.6 mmol) of benzenesulfonylacetonitrile and 6.55 g (30.3 mmol) of 1,4-dibromobutane in 50 ml of a 50% aqueous soda solution. The reaction mixture is stirred at room temperature for 3 h. It is then diluted with water and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over magnesium sulfate, filtered and the solvents are evaporated. The residue is purified on silica gel (heptane/ethyl acetate, 50/50, v/v). 6.35 g of 1-benzenesulfonyl-cyclopentanecarbonitrile is obtained in the form of a beige powder. (Yield=98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThey are dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvents are evaporated
  6. customThe residue is purified on silica gel (heptane/ethyl acetate, 50/50

Sources & evidence

ORD record
ord-8099e96b5e5041d1b9ce1a57a76f51e5
Source dataset
uspto-grants-2012_10
Patent number
US08283378B2

Reaction notes

Loading…