Lithium Bromide → 2-Bromo-6-isopropylnaphthalene

HRID 31558Notes

Reaction equation

HRID 31558 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:6]=[CH:5]2.[Br-].[Li+].[CH:22]([Mg]Br)([CH3:24])[CH3:23]>O1CCCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:22]([CH3:24])[CH3:23])[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 82050Lithium BromideHCID 153112166-Bromo-2-naphthyl TrifluoromethanesulfonateHCID 178418365HCID 178418365, compound

Product 1

HCID 235685312-Bromo-6-isopropylnaphthaleneYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

Under an atmospheric argon gas flow, trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol), dichloro(diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5% by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into three necked-flask equipped with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to −20° C. After slowly dripping isopropylmagnesiumbromide in an amount of 90 milliliter (90 mmol, 1 mol/liter (tetrahydrofuran)) into the flask, the resultant solution was stirred under heating at the temperature of 80° C. for 4 hours. After the reaction terminated, adding dilute hydrochloric acid in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium bicarbonate solution and sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=90/10), and as a result, 9.4 g of aimed compound (white crystal) was obtained (yield: 33%).

Workup

  1. customequipped
  2. temperaturewith cooling pipe
  3. customAfter the reaction terminated
  4. additionadding dilute hydrochloric acid in an amount of 100 milliliter into the reacted solution
  5. customan organic layer was separated
  6. washwashed with the use of sodium bicarbonate solution and sodium chloride solution
  7. dry with materialby drying with the use of magnesium sulfate
  8. customAfter removing the solvent
  9. distillationby distillation
  10. customby means of a rotary evaporator

Sources & evidence

ORD record
ord-bab819af325c4484a9d9b1d99e079973
Source dataset
uspto-grants-2008_09
Patent number
US07425653B2

Reaction notes

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