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Lithium Bromide → 2-Bromo-6-methylnaphthalene

HRID 31556
ノート
印刷プレビュー

反応式

HRID 31556 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 82050Lithium BromideHCID 153112166-Bromo-2-naphthyl TrifluoromethanesulfonateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 6405922-Bromo-6-methylnaphthalene収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-541a51d419e64e9b897a60307283e2e1
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07425653B2

反応ノート

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