Myristyl bromide → HCID 12517105, compound

HRID 1885889Notes

Reaction equation

HRID 1885889 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 169713-BromoanisoleHCID 5462224Magnesium

Product 1

HCID 12517105HCID 12517105, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 4.87 g portion of magnesium was placed in a two-necked round bottom flask. The flask was flamed several times and 37.4 g of m-bromoanisole and 200 ml of tetrahydrofuran were added. As soon as the reaction stopped it was refluxed for 1 hour and then added to a boiling solution of 52.68 g of tetradecyl bromide in tetrahydrofuran. Then 10 ml of lithium cupric chloride was added and the mixture was refluxed for 1.25 hours, stirred at room temperature for 16 hours, quenched with water, washed with ammonium chloride solution, brine, dried and the solvent removed. The resulting oily residue was distilled in a Kugelrohr apparatus giving 52.4 g of the desired compound as a clear oil, B. P. (120°/0.5 mm).

Workup

  1. additionwere added
  2. temperaturewas refluxed for 1 hour
  3. temperaturethe mixture was refluxed for 1.25 hours
  4. customquenched with water
  5. washwashed with ammonium chloride solution, brine
  6. customdried
  7. customthe solvent removed
  8. distillationThe resulting oily residue was distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-83b808bccc004374a9bbafdc7f0e1345
Source dataset
uspto-grants-1992_09
Patent number
US05147864

Reaction notes

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