1,2-Dibromoethane → HCID 20565008, compound

HRID 224510Notes

Reaction equation

HRID 224510 reaction equation
[Mg].[CH2:2](Br)[C:3]#[CH:4].BrCCBr.[CH2:10]=[C:11]([CH2:14][CH2:15][CH3:16])[CH:12]=[O:13].[Cl-].[NH4+]>CCOCC>[OH:13][CH:12]([C:11](=[CH2:10])[CH2:14][CH2:15][CH3:16])[CH2:4][C:3]#[CH:2]

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 7842Propargyl bromide2×HCID 25517Ammonium ChlorideHCID 706092-MethylenepentanalHCID 5462224Magnesium

Product 1

HCID 20565008HCID 20565008, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 12.16 g. of magnesium in 120 ml. of ether containing 200 mg. of mercuric chloride is added 2 ml. of propargyl bromide and 0.5 ml. of 1,2-dibromoethane. This mixture is stirred under argon until the reaction begins. To this is added with stirring a solution of 41.57 g. of 2-methylene valeraldehyde and 64.95 g. of propargyl bromide in 90 ml. of ether, dropwise, at a rate to maintain reflux. After addition is complete the mixture is refluxed 15 minutes, stirred at room temperature one hour, cooled to 0° C. and saturated ammonium chloride solution is added dropwise until reflux stops. The mixture is filtered through Celite, dried over magnesium sulfate and the ether is removed giving the product as a light orange oil.

Workup

  1. additionTo a stirred mixture of 12.16 g
  2. additionTo this is added
  3. stirringwith stirring a solution of 41.57 g
  4. temperaturereflux
  5. additionAfter addition
  6. temperatureis refluxed 15 minutes
  7. stirringstirred at room temperature one hour
  8. temperatureuntil reflux
  9. filtrationThe mixture is filtered through Celite
  10. dry with materialdried over magnesium sulfate
  11. customthe ether is removed

Sources & evidence

ORD record
ord-2b50041a367a469da397523184c3a249
Source dataset
uspto-grants-1980_11
Patent number
US04232166

Reaction notes

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