Hydrochloric Acid → HCID 15419321, compound

HRID 1534690Notes

Reaction equation

HRID 1534690 reaction equation
[Mg].Br[CH2:3][CH2:4][CH:5]=[CH2:6].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.Cl>O1CCCC1>[CH2:12]([C:11]1[CH:14]=[CH:15][C:8]([Br:7])=[CH:9][CH:10]=1)[CH2:6][CH2:5][CH:4]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21241Homoallyl bromideHCID 685274-Bromobenzyl bromideHCID 5462224Magnesium

Product 1

HCID 15419321HCID 15419321, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 970 mg of magnesium in 20 ml of tetrahydrofuran was added dropwise a solution of 5.4 g of 4-bromo-1-butene in 20 ml of tetrahydrofuran while keeping at 50° C. Then, a solution of 10.0 g of 4-bromobenzyl bromide in 20 ml of tetrahydrofuran was added dropwise slowly, and the mixture was refluxed for an hour, made acidic with dilute hydrochloric acid and extracted with n-hexane. The organic layer was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was chromatographed on silica gel column with n-hexane to give 1.14 g of 4-(4-pentenyl)bromobenzene.

Workup

  1. customwhile keeping at 50° C
  2. temperaturethe mixture was refluxed for an hour
  3. extractionextracted with n-hexane
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was chromatographed on silica gel column with n-hexane

Sources & evidence

ORD record
ord-6b3f2096fc464d0187b9b4aa9961939d
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

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