Lithium Bromide → 2-Bromo-6-methylnaphthalene

HRID 31556

반응식

HRID 31556 반응식
[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+].[CH3:22][Mg]Br>O1CCCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 82050Lithium BromideHCID 153112166-Bromo-2-naphthyl TrifluoromethanesulfonateHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 6405922-Bromo-6-methylnaphthalene수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
80 °C

실험 절차

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 a three neck flask with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to −20° C. After slowly dripping methylmagnesiumbromide 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: 47%).

후처리

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

출처 및 근거

ORD 기록
ord-541a51d419e64e9b897a60307283e2e1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425653B2

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