1-Pentene, 5-bromo- → Bis(3-butenyl)mercury

HRID 1030286Notes

Reaction equation

HRID 1030286 reaction equation
[CH2:1]([Hg:6][CH2:7][CH2:8][CH2:9][CH:10]=C)[CH2:2][CH2:3][CH:4]=C.C([Mg]Br)CCC=C.BrCCCC=C.[Mg]>O1CCCC1.O>[CH2:1]([Hg:6][CH2:7][CH2:8][CH:9]=[CH2:10])[CH2:2][CH:3]=[CH2:4]

Participants

7

Reactant 4

HCID 707041-Pentene, 5-bromo-HCID 5462224MagnesiumHCID 19105421Di(pent-4-en-1-yl)mercuryHCID 178445862HCID 178445862, compound

Product 1

HCID 12533408Bis(3-butenyl)mercuryYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Preparation of bis(4-pentenyl)mercury: To a solution of 4-pentenyl magnesium bromide, prepared from 25 g of 1-bromo-4-pentene (169 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 50 mL of tetrahydrofuran. After stirring for 2 hours at 60° C., the reaction mixture was hydrolyzed with water at 0°-5° C. The organic layer was separated from aqueous layer; the product was distilled to give bis-3-butenyl mercury in 67% yield. The identity of the compound was confirmed by gas chromatography and 1H NMR.

Workup

  1. additionwas added dropwise at 50° C.
  2. customThe organic layer was separated from aqueous layer
  3. distillationthe product was distilled

Sources & evidence

ORD record
ord-600abf639513445cbafc104f778c6e93
Source dataset
uspto-grants-1992_04
Patent number
US05104952

Reaction notes

Loading…