Homoallyl bromide → Bisbutenyl mercury

HRID 1613115Notes

Reaction equation

HRID 1613115 reaction equation
[CH2:1]([Hg:5][CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:2][CH:3]=[CH2:4].C([Mg]Br)CC=C.BrCCC=C.[Mg]>O1CCCC1.O>[CH:1]([Hg:5][CH:6]=[CH:7][CH2:8][CH3:9])=[CH:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 21241Homoallyl bromideHCID 5462224MagnesiumHCID 12533408Bis(3-butenyl)mercuryHCID 178418797HCID 178418797, compound

Product 1

HCID 86745677Bisbutenyl mercuryYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation of bis(3-butenyl)mercury: To a solution of 3-butenylmagnesium bromide, prepared from 25 g of 1-bromo-3-butene (187 mmole) and 5 g of magnesium (208 mmole) in 40 mL of tetrahydrofuran, was added dropwise, at 50° C. with stirring, a solution of 25.2 g of mercuric chloride (93 mmole) in tetrahydrofuran. After stirring for 2 hours at 60° C., the reaction mixture was hydrolyzed with water at 0°-5° C. Organic layer was separated from aqueous layer; the product was distilled to give bisbutenyl mercury in 60% yield. The yield of the desired product was confirmed by gas chromatography (GC) and 1H NMR.

Workup

  1. additionwas added dropwise, at 50° C.
  2. stirringAfter stirring for 2 hours at 60° C.
  3. customOrganic layer was separated from aqueous layer
  4. distillationthe product was distilled

Sources & evidence

ORD record
ord-c734b09e9cf34009a087b33304658c33
Source dataset
uspto-grants-1993_03
Patent number
US05192616

Reaction notes

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