Magnesium Bromide → (6Z,9Z)-18-bromooctadeca-6,9-diene

HRID 2273370Notes

Reaction equation

HRID 2273370 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=O)=O.[Br-:24].[Mg+2].[Br-]>CCOCC>[CH2:6]([Br:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 82241Magnesium BromideHCID 59753235Linoleyl methanesulfonate

Product 1

HCID 10065142(6Z,9Z)-18-bromooctadeca-6,9-dieneYield 97.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Linoleyl methanesulfonate (27 g, 78 mmoles), anhydrous magnesium bromide (43 g; 238 mmoles), and 1000 ml of dry ether was placed in a 2500 ml three-necked flask equipped with reflux condenser, inlet and outlet tubes for dry nitrogen, and mechanical stirrer. The mixture was stirred vigorously at room temperature for 24 hr. More ether, and cold, degassed water were added after 24 hours. The water layer was extracted twice with ether. The combined ether phases were washed consecutively with water, 1% potassium carbonate solution, and water, and are dried over anhydrous sodium sulfate. Concentration of the ether phase using a rotary evaporator yielded 25 g (97%) of linoleyl bromide; mp −35° C.

Workup

  1. customequipped
  2. temperaturewith reflux condenser, inlet and outlet tubes for dry nitrogen, and mechanical stirrer
  3. customMore ether, and cold, degassed water
  4. additionwere added after 24 hours
  5. extractionThe water layer was extracted twice with ether
  6. washThe combined ether phases were washed consecutively with water, 1% potassium carbonate solution, and water
  7. dry with materialare dried over anhydrous sodium sulfate
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-c9e178e7c7854455a971876a047afc75
Source dataset
uspto-grants-2015_09
Patent number
US09120938B2

Reaction notes

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