1-Octene → 1-Octenyl bromomethyl sulfone

HRID 364248

Reaction equation

HRID 364248 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:9][CH2:10][S:11](Br)(=[O:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[Br:9][CH2:10][S:11]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 81251-OcteneHCID 11430Potassium CarbonateHCID 10977482Bromomethanesulfonyl bromide

Product 1

HCID 543748991-Octenyl bromomethyl sulfoneYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-octene (2.82 g) and bromomethanesulfonyl bromide (6.0 g) in methylene chloride (4 mL) was irradiated at -20° C. with an ultraviolet lamp for 0.5 hours. A small amount of solid potassium carbonate was added and then removed by filtration. The reaction mixture was diluted with methylene chloride (50 mL), cooled in ice and treated with a solution of triethylamine (4.45 g) in 10 mL of methylene chloride. The reaction mixture was stirred for 0.25 hours and was washed with dilute HCl and water. The methylene chloride layer was separated, dried over anhydrous magnesium sulfate and the methylene chloride removed in vacuo to give 5.9 g (97% yield) of oily 1-octenyl bromomethyl sulfone which was characterized by IR and NMR spectroscopy.

Workup

  1. customwas irradiated at -20° C. with an ultraviolet lamp for 0.5 hours
  2. customremoved by filtration
  3. additionThe reaction mixture was diluted with methylene chloride (50 mL)
  4. temperaturecooled in ice
  5. additiontreated with a solution of triethylamine (4.45 g) in 10 mL of methylene chloride
  6. washwas washed with dilute HCl and water
  7. customThe methylene chloride layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe methylene chloride removed in vacuo

Sources & evidence

ORD record
ord-6d2a5b4874154d878d83e69241480c1f
Source dataset
uspto-grants-1986_08
Patent number
US04604480

Linked notes

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