Bis(2-bromoethyl) ether → 4-(3,4-Dichlorophenyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1868788Notes

Reaction equation

HRID 1868788 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.[H-].[Na+]>CCOCC.CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 431642774-(3,4-Dichlorophenyl)tetrahydro-2H-pyran-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

3,4-Dichlorophenylacetonitrile (10.00 g, 53.8 mmol) and bis(2-bromoethyl)ether (12.5 g, 53.8 mmol) were dissolved in ether and added dropwise via addition funnel to a suspension of NaH (60% dispersion in mineral oil; 6.45 g, 161 mmol) in 1-methylpyrrolidone (108 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and was then allowed to warm to ambient temperature. The reaction was then quenched with water. 5N HCl was added, and the reaction mixture was diluted with 200 mL of diethyl ether, added to a separatory funnel, washed 2 times with 100 mL of ether, separated, dried over Na2SO4, and concentrated in vacuo to give the purified title compound (7.97 g) after flash chromatography.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe reaction was then quenched with water
  3. addition5N HCl was added
  4. additionthe reaction mixture was diluted with 200 mL of diethyl ether
  5. additionadded to a separatory funnel
  6. washwashed 2 times with 100 mL of ether
  7. customseparated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto give the
  11. custompurified title compound (7.97 g) after flash chromatography

Sources & evidence

ORD record
ord-dc02538a3526419ab065b259cb1d372a
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…