Dibromomethane → HCID 14822515, compound

HRID 2073894Notes

Reaction equation

HRID 2073894 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[C:9]#[N:10])=[CH:4][CH:3]=1.[CH2:15](Br)[Br:16].[OH-].[Na+]>CS(C)=O>[Br:16][CH2:15][C:8]([C:9]#[N:10])([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 11041961Benzeneacetonitrile, .alpha.-butyl-4-chloro-

Product 1

HCID 14822515HCID 14822515, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 300 ml three neck flask fitted with a mechanical stirrer, thermometer and addition funnel was added 20.8 gm (0.1 mol) of (p-chlorophenyl)hexanenitrile, 34.8 gm (0.2 mol) of methylene bromide and 50 ml of DMSO. To the reaction flask was added 24 ml of 50% (w/w) sodium hydroxide, dropwise over a 35 minute period. Upon completion of the reaction, it was quenched by adding 500 ml of water. The aqueous mixture was extracted three times with ether, then the combined ether extracts were washed three times with water and once with brine. The organic phase was dried over sodium sulfate, filtered and the solvent removed by rotary evaporation yielding 22.6 gm of a yellow oil.

Workup

  1. additionthermometer and addition funnel
  2. customUpon completion of the reaction, it
  3. customwas quenched
  4. additionby adding 500 ml of water
  5. extractionThe aqueous mixture was extracted three times with ether
  6. washthe combined ether extracts were washed three times with water
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-92dd88547df44dad9f551cfc0c508340
Source dataset
uspto-grants-1990_04
Patent number
US04920139

Reaction notes

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