2-Pentanone → 1-Bromo-trans-1-octen-3-one

HRID 1903967Notes

Reaction equation

HRID 1903967 reaction equation
Cl/[CH:2]=[CH:3]/[C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Br-:11].[Li+].CC(=O)CCC>>[Br:11]/[CH:2]=[CH:3]/[C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 78952-PentanoneHCID 82050Lithium BromideHCID 110410031-Chloro-trans-1-octen-3-one

Product 1

HCID 117903381-Bromo-trans-1-octen-3-one

Procedure

A mixture of 68.0 g. (0.424 mole) of 1-chloro-trans-1-octen-3 one (Example 723) and 444 g. (4.24 moles) of anhydrous lithium bromide in 900 ml. of 2-pentanone is refluxed for 30 minutes, cooled, and partitioned between ice water and ether. The organic phase is washed with water and saturated brine, dried (NaSO4), and evaporated to an oil. This material is used directly without purification.

Workup

  1. additionA mixture of 68.0 g
  2. temperaturecooled
  3. custompartitioned between ice water and ether
  4. washThe organic phase is washed with water and saturated brine
  5. dry with materialdried (NaSO4)
  6. customevaporated to an oil
  7. customThis material is used directly without purification

Sources & evidence

ORD record
ord-929da8a94586423db6d79211480cf6f4
Source dataset
uspto-grants-1984_03
Patent number
US04439365

Reaction notes

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