Iodine → 1-Bromo-4-iodonaphthalene

HRID 931857ノート

反応式

HRID 931857 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Br)=[CH:4][CH:3]=1.[Li]CCCC.[I:18]I.OS([O-])=O.[Na+]>C1COCC1>[I:18][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][CH:4]=1

参加物

6

反応物 4

HCID 807IodineHCID 665211,4-DibromonaphthaleneHCID 23665763Sodium BisulfiteHCID 178418339Butyllithium

生成物 1

HCID 50736671-Bromo-4-iodonaphthalene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

100 g (350 mmol) of 1,4-dibromonaphthalene are initially introduced in 11 of THF, cooled to −70° C., and 235 ml of n-BuLi (1.6 M in hexane, 370 mmol) are added dropwise. After 1 h, 103 g (406 mmol) of I2 in 250 ml of THF are added dropwise, the mixture is stirred at −70° C. for a further 2 h, warmed to 0° C. and quenched by the addition of 50 ml (644 mmol) of aqueous NaHSO3 solution (w=39%). The phases are separated, and the aqueous phase is extracted once with MTB. The combined organic phases are washed with saturated sodium chloride soln., dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol, giving 1-iodo-4-bromonaphthalene as a yellow solid.

後処理

  1. temperaturewarmed to 0° C.
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted once with MTB
  4. washThe combined organic phases are washed with saturated sodium chloride soln
  5. dry with material, dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customThe residue is purified by column chromatography (SiO2, heptane)
  9. customthe further purification
  10. customis carried out by recrystallisation from isopropanol

出典と根拠

ORDレコード
ord-f0fbc23357924075aa3d1252886ca745
出典データセット
uspto-grants-2016_03
特許番号
US09296948B2

反応ノート

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