Hexane → HCID 86651382, compound

HRID 1949183Notes

Reaction equation

HRID 1949183 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.CCCCCC.C([Li])CCC.Cl[P:21]([C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1>O1CCCC1>[CH3:28][C:25]1[CH:24]=[CH:23][C:22]([P:21]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 792052-Bromo-6-methylpyridineHCID 4188608BIS(4-METHYLPHENYL)CHLOROPHOSPHINEHCID 178418339Butyllithium

Product 1

HCID 86651382HCID 86651382, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After dissolving 2-bromo-6-methylpyridine (23.5 mmol) in 40 ml of tetrahydrofuran, the mixture was cooled in a dry ice-ethanol bath, 1.59 M hexane solution of n-butyllithium (23.5 mmol) was added dropwise while stirring, and stirring was continued for 10 minutes to obtain a reaction mixture. To the obtained reaction mixture there was added chlorobis(4-methylphenyl)phosphine (17.5 mmol) dissolved in 40 ml of tetrahydrofuran, and stirring was continued at room temperature for 2 hours. The reaction solution was quenched with water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, purification was performed twice by silica gel column chromatography (developing solution: hexane/ethyl acetate=5/1, 9/1), to obtain 2.68 g of bis(4-methylphenyl)(6-methyl-2-pyridyl)phosphine (50% yield).

Workup

  1. temperaturethe mixture was cooled in a dry ice-ethanol bath
  2. stirringstirring
  3. customto obtain a reaction mixture
  4. customTo the obtained reaction mixture there
  5. stirringstirring
  6. waitwas continued at room temperature for 2 hours
  7. customThe reaction solution was quenched with water
  8. extractionextracted with ethyl acetate
  9. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  10. distillationAfter distilling off the solvent
  11. customunder reduced pressure, purification

Sources & evidence

ORD record
ord-3c2199de5b7547c6968b9214967c5938
Source dataset
uspto-grants-2013_03
Patent number
US08399699B2

Reaction notes

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