1-Bromo-2-Chloroethane → HCID 86741981, compound

HRID 2414077Notes

Reaction equation

HRID 2414077 reaction equation
C([Li])CCC.C(NCC)C.[CH2:11]([CH:14]([CH2:17][CH2:18][CH3:19])[C:15]#[N:16])[CH2:12][CH3:13].Br[CH2:21][CH2:22][Cl:23]>CCCCCC.CCOCC.O>[Cl:23][CH2:22][CH2:21][C:14]([CH2:17][CH2:18][CH3:19])([CH2:11][CH2:12][CH3:13])[C:15]#[N:16]

Participants

8

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 8021DiethylamineHCID 833302-PropylvaleronitrileHCID 178418339Butyllithium

Product 1

HCID 86741981HCID 86741981, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

To the solution (245 ml) of 1,6M n butyllithium in hexane is added, drop by drop in an atmosphere of nitrogen and with stirring, the solution of 28.8 g of diethylamine in 100 ml of anhydrous ether. After 1 hour, the solution of 49.2 g of 2-propyl pentane nitrile in 100 ml of anhydrous ether is added at ambient temperature then, after return to ambient temperature, the solution of 49.1 g of 1-bromo 2-chloro ethane in 700 ml of anhydrous ether is added. The mixture is taken to reflux for 15 hours then, whilst cooling the reaction mixture in an ice bath, water is added. The organic phase is separated, washed with water, then with a dilute solution of hydrochloric acid and again with water. It is dried over sodium sulfate and the solvent is evaporated. The residue is distilled and a liquid is obtained; b.p./20 mm Hg: 140°-150° C.

Workup

  1. temperatureto reflux for 15 hours
  2. temperaturewhilst cooling the reaction mixture in an ice bath
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialIt is dried over sodium sulfate
  6. customthe solvent is evaporated
  7. distillationThe residue is distilled
  8. customa liquid is obtained
  9. custom140°-150° C.

Sources & evidence

ORD record
ord-c1dc846746ee4ceabfa96141e679cd84
Source dataset
uspto-grants-1988_01
Patent number
US04721710

Reaction notes

Loading…